5-methyl-2-propan-2-ylaniline

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Isopropyl-5-methylaniline (286 g, 1.91 mol) and sodium bicarbonate (270 g, 3.22 mol) were charged in to a round bottomed flask with stirring under nitrogen atmosphere and cooled to 0-5° C. 2-Chloroacetyl chloride (218 g, 1.93 mol) was added drop wise at 0-5° C. over a period of 1 hour. The reaction was stirred at 0-5° C. for 1 hour. After completion of the reaction, purified water (2.86 L) was added and stirred at 25-30° C. for 15 minutes. The layers were then separated. The organic layer was washed with water (2×2.86 L) and with brine (1.43 L). The aqueous layers were combined and extracted with ethyl acetate (1.43 L). The organic layers were dried with sodium sulphate, filtered, and concentrated at 50-55° C. under vacuum (500-600 mm Hg) to ⅖ths volume. Hexanes (2.86 L) were added and the mixture was stirred at 25-30° C. for 1 hour. The solid was filtered, washed with hexanes (1.43 L), and dried at 45-50° C. under vacuum (500-600 mm Hg) to give 2-chloro-N-(2-isopropyl-5-methylphenyl)acetamide as an off-white solid (270 g, 66%): mp 97-99° C., 1H NMR (300 MHz, CDCl3) δ 8.27 (s, 1H), 7.60 (s, 1H), 7.20 (d, J=7.95 Hz, 1H), 7.04 (d, J=7.89 Hz, 1H), 4.25 (s, 2H), 2.99 (q, J=6.78 Hz, 1H), 2.34 (s, 3H), 1.26 (d, J=6.84 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 164.07, 137.28, 136.33, 132.95, 127.35, 125.62, 124.46, 43.21, 27.86, 22.98, 21.00; ESIMS m/z 226 ([M+H]+). The reaction was stirred at 0-5° C. for 1 hour After completion of the reaction purified water (2.86 L) was added stirred at 25-30° C. for 15 minutes The layers were then separated The organic layer was washed with water (2×2.86 L) and with brine (1.43 L) extracted with ethyl acetate (1.43 L) The organic layers were dried with sodium sulphate filtered concentrated at 50-55° C. under vacuum (500-600 mm Hg) to ⅖ths volume Hexanes (2.86 L) were added the mixture was stirred at 25-30° C. for 1 hour The solid was filtered washed with hexanes (1.43 L) dried at 45-50° C. under vacuum (500-600 mm Hg)

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Isopropyl-5-methylaniline (286 g, 1.91 mol) and sodium bicarbonate (270 g, 3.22 mol) were charged in to a round bottomed flask with stirring under nitrogen atmosphere and cooled to 0-5° C. 2-Chloroacetyl chloride (218 g, 1.93 mol) was added drop wise at 0-5° C. over a period of 1 hour. The reaction was stirred at 0-5° C. for 1 hour. After completion of the reaction, purified water (2.86 L) was added and stirred at 25-30° C. for 15 minutes. The layers were then separated. The organic layer was washed with water (2×2.86 L) and with brine (1.43 L). The aqueous layers were combined and extracted with ethyl acetate (1.43 L). The organic layers were dried with sodium sulphate, filtered, and concentrated at 50-55° C. under vacuum (500-600 mm Hg) to ⅖ths volume. Hexanes (2.86 L) were added and the mixture was stirred at 25-30° C. for 1 hour. The solid was filtered, washed with hexanes (1.43 L), and dried at 45-50° C. under vacuum (500-600 mm Hg) to give 2-chloro-N-(2-isopropyl-5-methylphenyl)acetamide as an off-white solid (270 g, 66%): mp 97-99° C., 1H NMR (300 MHz, CDCl3) δ 8.27 (s, 1H), 7.60 (s, 1H), 7.20 (d, J=7.95 Hz, 1H), 7.04 (d, J=7.89 Hz, 1H), 4.25 (s, 2H), 2.99 (q, J=6.78 Hz, 1H), 2.34 (s, 3H), 1.26 (d, J=6.84 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 164.07, 137.28, 136.33, 132.95, 127.35, 125.62, 124.46, 43.21, 27.86, 22.98, 21.00; ESIMS m/z 226 ([M+H]+). The reaction was stirred at 0-5° C. for 1 hour After completion of the reaction purified water (2.86 L) was added stirred at 25-30° C. for 15 minutes The layers were then separated The organic layer was washed with water (2×2.86 L) and with brine (1.43 L) extracted with ethyl acetate (1.43 L) The organic layers were dried with sodium sulphate filtered concentrated at 50-55° C. under vacuum (500-600 mm Hg) to ⅖ths volume Hexanes (2.86 L) were added the mixture was stirred at 25-30° C. for 1 hour The solid was filtered washed with hexanes (1.43 L) dried at 45-50° C. under vacuum (500-600 mm Hg)

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Isopropyl-5-methylaniline (286 g, 1.91 mol) and sodium bicarbonate (270 g, 3.22 mol) were charged in to a round bottomed flask with stirring under nitrogen atmosphere and cooled to 0-5° C. 2-Chloroacetyl chloride (218 g, 1.93 mol) was added drop wise at 0-5° C. over a period of 1 hour. The reaction was stirred at 0-5° C. for 1 hour. After completion of the reaction, purified water (2.86 L) was added and stirred at 25-30° C. for 15 minutes. The layers were then separated. The organic layer was washed with water (2×2.86 L) and with brine (1.43 L). The aqueous layers were combined and extracted with ethyl acetate (1.43 L). The organic layers were dried with sodium sulphate, filtered, and concentrated at 50-55° C. under vacuum (500-600 mm Hg) to 2/5ths volume. Hexanes (2.86 L) were added and the mixture was stirred at 25-30° C. for 1 hour. The solid was filtered, washed with hexanes (1.43 L), and dried at 45-50° C. under vacuum (500-600 mm Hg) to give 2-chloro-N-(2-isopropyl-5-methylphenyl)acetamide as an off-white solid (270 g, 66%): mp 97-99° C.; 1H NMR (300 MHz, CDCl3) δ 8.27 (s, 1H), 7.60 (s, 1H), 7.20 (d, J=7.95 Hz, 1H), 7.04 (d, J=7.89 Hz, 1H), 4.25 (s, 2H), 2.99 (q, J=6.78 Hz, 1H), 2.34 (s, 3H), 1.26 (d, J=6.84 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 164.07, 137.28, 136.33, 132.95, 127.35, 125.62, 124.46, 43.21, 27.86, 22.98, 21.00; ESIMS m/z 226 ([M+H]+). The reaction was stirred at 0-5° C. for 1 hour After completion of the reaction purified water (2.86 L) was added stirred at 25-30° C. for 15 minutes The layers were then separated The organic layer was washed with water (2×2.86 L) and with brine (1.43 L) extracted with ethyl acetate (1.43 L) The organic layers were dried with sodium sulphate filtered concentrated at 50-55° C. under vacuum (500-600 mm Hg) to 2/5ths volume Hexanes (2.86 L) were added the mixture was stirred at 25-30° C. for 1 hour The solid was filtered washed with hexanes (1.43 L) dried at 45-50° C. under vacuum (500-600 mm Hg)

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-isopropyl-5-methylaniline (1.0 g, 6.7 mmol) in a 25 mL vial equipped with a stir bar, Vigreux column, and nitrogen was added carbon disulfide (3.0 mL, 50 mmol). The reaction was heated to 40° C. and cooled immediately. To this solution was added triethylamine (0.93 mL, 6.7 mmol). The reaction was heated to 50° C. for 90 minutes and cooled to room temperature overnight. The reaction mixture was transferred to a 100 mL round-bottomed flask and concentrated. The residue was taken up in acetonitrile (33.5 mL) and treated with N,N′-diisopropycarbodiimide (1.04 mL, 6.70 mmol). The reaction was stopped after a few h and concentrated. Purification by flash column chromatography using 2.5-5% ethyl acetate/hexanes as eluent provided a mixture of products. Re-purification by reversed phase column chromatography using 5-100% acetonitrile/water as eluent provided the title compound (65% in dichloromethane, 0.62 g, 31%), which was used without further purification: IR (thin film) 2963 (m), 2924 (m), 2869 (w), 2089 (vs), 1611 (w), 1501 (m) cm−1; 1H NMR (300 MHz, CDCl3) δ 7.16 (d, J=8.6 Hz, 1H), 7.09-7.03 (m, 2H), 3.19 (h, J=6.8 Hz, 1H), 2.30 (s, 3H), 1.24 (d, J=6.9 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 141.50, 136.70, 134.59, 128.84, 128.58, 127.12, 126.05, 29.20, 22.83, 20.62. cooled immediately The reaction was heated to 50° C. for 90 minutes cooled to room temperature overnight The reaction mixture was transferred to a 100 mL round-bottomed flask concentrated concentrated Purification by flash column chromatography provided a mixture of products

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 4-methyl-2-nitro-1-(prop-1-en-2-yl)benzene (0.986 g, 5.56 mmol) in a 100 mL round-bottomed flask equipped with a stir bar was added ethyl acetate (55.6 mL) and palladium on carbon (1.18 g, 0.556 mmol). The reaction was evacuated and backfilled with hydrogen (balloon). The reaction was stirred under an atmosphere of hydrogen overnight. The reaction mixture was filtered through a pad of Celite® and concentrated providing the title compound as a clear and colorless oil (0.788 g, 95%): IR (thin film) 3464 (m), 3372 (m), 3011 (m), 2959 (s), 2869 (m), 1621 (m), 1575 (m), 1509 (m) cm−1; 1H NMR (400 MHz, CDCl3) δ 7.03 (d, J=7.8 Hz, 1H), 6.61 (dd, J=7.8, 1.7 Hz, 1H), 6.54-6.50 (m, 1H), 3.59 (bs, 2H), 2.87 (hept, J=6.8 Hz, 1H), 2.24 (s, 3H), 1.24 (d, J=6.8 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 143.14, 136.16, 129.82, 125.33, 119.79, 116.55, 99.97, 27.36, 22.41, 20.96. The reaction was evacuated The reaction mixture was filtered through a pad of Celite® concentrated

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-isopropyl-5-methylaniline (1.0 g, 6.7 mmol) in a 25 mL vial equipped with a stir bar, Vigreux column, and nitrogen was added carbon disulfide (3.0 mL, 50 mmol). The reaction was heated to 40° C. and cooled immediately. To this solution was added triethylamine (0.93 mL, 6.7 mmol). The reaction was heated to 50° C. for 90 minutes and cooled to room temperature overnight. The reaction mixture was transferred to a 100 mL round-bottomed flask and concentrated. The residue was taken up in acetonitrile (33.5 mL) and treated with N,N′-diisopropycarbodiimide (1.04 mL, 6.70 mmol). The reaction was stopped after a few h and concentrated. Purification by flash column chromatography using 2.5-5% ethyl acetate/hexanes as eluent provided a mixture of products. Re-purification by reversed phase column chromatography using 5-100% acetonitrile/water as eluent provided the title compound (65% in dichloromethane, 0.62 g, 31%), which was used without further purification: IR (thin film) 2963 (m), 2924 (m), 2869 (w), 2089 (vs), 1611 (w), 1501 (m) cm−1; 1H NMR (300 MHz, CDCl3) δ 7.16 (d, J=8.6 Hz, 1H), 7.09-7.03 (m, 2H), 3.19 (h, J=6.8 Hz, 1H), 2.30 (s, 3H), 1.24 (d, J=6.9 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 141.50, 136.70, 134.59, 128.84, 128.58, 127.12, 126.05, 29.20, 22.83, 20.62. cooled immediately The reaction was heated to 50° C. for 90 minutes cooled to room temperature overnight The reaction mixture was transferred to a 100 mL round-bottomed flask concentrated concentrated Purification by flash column chromatography provided a mixture of products

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 4-methyl-2-nitro-1-(prop-1-en-2-yl)benzene (0.986 g, 5.56 mmol) in a 100 mL round-bottomed flask equipped with a stir bar was added ethyl acetate (55.6 mL) and palladium on carbon (1.18 g, 0.556 mmol). The reaction was evacuated and backfilled with hydrogen (balloon). The reaction was stirred under an atmosphere of hydrogen overnight. The reaction mixture was filtered through a pad of Celite® and concentrated providing the title compound as a clear and colorless oil (0.788 g, 95%): IR (thin film) 3464 (m), 3372 (m), 3011 (m), 2959 (s), 2869 (m), 1621 (m), 1575 (m), 1509 (m) cm−1; 1H NMR (400 MHz, CDCl3) δ 7.03 (d, J=7.8 Hz, 1H), 6.61 (dd, J=7.8, 1.7 Hz, 1H), 6.54-6.50 (m, 1H), 3.59 (bs, 2H), 2.87 (hept, J=6.8 Hz, 1H), 2.24 (s, 3H), 1.24 (d, J=6.8 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 143.14, 136.16, 129.82, 125.33, 119.79, 116.55, 99.97, 27.36, 22.41, 20.96. The reaction was evacuated The reaction mixture was filtered through a pad of Celite® concentrated

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Isopropyl-5-methylaniline (286 g, 1.91 mol) and sodium bicarbonate (270 g, 3.22 mol) were charged in to a round bottomed flask with stirring under nitrogen atmosphere and cooled to 0-5° C. 2-Chloroacetyl chloride (218 g, 1.93 mol) was added drop wise at 0-5° C. over a period of 1 hour. The reaction was stirred at 0-5° C. for 1 hour. After completion of the reaction, purified water (2.86 L) was added and stirred at 25-30° C. for 15 minutes. The layers were then separated. The organic layer was washed with water (2×2.86 L) and with brine (1.43 L). The aqueous layers were combined and extracted with ethyl acetate (1.43 L). The organic layers were dried with sodium sulphate, filtered, and concentrated at 50-55° C. under vacuum (500-600 mm Hg) to ⅖ths volume. Hexanes (2.86 L) were added and the mixture was stirred at 25-30° C. for 1 hour. The solid was filtered, washed with hexanes (1.43 L), and dried at 45-50° C. under vacuum (500-600 mm Hg) to give 2-chloro-N-(2-isopropyl-5-methylphenyl)acetamide as an off-white solid (270 g, 66%): mp 97-99° C.; 1H NMR (300 MHz, CDCl3) δ 8.27 (s, 1H), 7.60 (s, 1H), 7.20 (d, J=7.95 Hz, 1H), 7.04 (d, J=7.89 Hz, 1H), 4.25 (s, 2H), 2.99 (q, J=6.78 Hz, 1H), 2.34 (s, 3H), 1.26 (d, J=6.84 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 164.07, 137.28, 136.33, 132.95, 127.35, 125.62, 124.46, 43.21, 27.86, 22.98, 21.00; ESIMS m/z 226 ([M+H]+). The reaction was stirred at 0-5° C. for 1 hour After completion of the reaction purified water (2.86 L) was added stirred at 25-30° C. for 15 minutes The layers were then separated The organic layer was washed with water (2×2.86 L) and with brine (1.43 L) extracted with ethyl acetate (1.43 L) The organic layers were dried with sodium sulphate filtered concentrated at 50-55° C. under vacuum (500-600 mm Hg) to ⅖ths volume Hexanes (2.86 L) were added the mixture was stirred at 25-30° C. for 1 hour The solid was filtered washed with hexanes (1.43 L) dried at 45-50° C. under vacuum (500-600 mm Hg)

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Isopropyl-5-methylaniline (286 g, 1.91 mol) and sodium bicarbonate (270 g, 3.22 mol) were charged in to a round bottomed flask with stirring under nitrogen atmosphere and cooled to 0-5° C. 2-Chloroacetyl chloride (218 g, 1.93 mol) was added drop wise at 0-5° C. over a period of 1 hour. The reaction was stirred at 0-5° C. for 1 hour. After completion of the reaction, purified water (2.86 L) was added and stirred at 25-30° C. for 15 minutes. The layers were then separated. The organic layer was washed with water (2×2.86 L) and with brine (1.43 L). The aqueous layers were combined and extracted with ethyl acetate (1.43 L). The organic layers were dried with sodium sulphate, filtered, and concentrated at 50-55° C. under vacuum (500-600 mm Hg) to ⅖ths volume. Hexanes (2.86 L) were added and the mixture was stirred at 25-30° C. for 1 hour. The solid was filtered, washed with hexanes (1.43 L), and dried at 45-50° C. under vacuum (500-600 mm Hg) to give 2-chloro-N-(2-isopropyl-5-methylphenyl)acetamide as an off-white solid (270 g, 66%): mp 97-99° C., 1H NMR (300 MHz, CDCl3) δ 8.27 (s, 1H), 7.60 (s, 1H), 7.20 (d, J=7.95 Hz, 1H), 7.04 (d, J=7.89 Hz, 1H), 4.25 (s, 2H), 2.99 (q, J=6.78 Hz, 1H), 2.34 (s, 3H), 1.26 (d, J=6.84 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 164.07, 137.28, 136.33, 132.95, 127.35, 125.62, 124.46, 43.21, 27.86, 22.98, 21.00; ESIMS m/z 226 ([M+H]+). The reaction was stirred at 0-5° C. for 1 hour After completion of the reaction purified water (2.86 L) was added stirred at 25-30° C. for 15 minutes The layers were then separated The organic layer was washed with water (2×2.86 L) and with brine (1.43 L) extracted with ethyl acetate (1.43 L) The organic layers were dried with sodium sulphate filtered concentrated at 50-55° C. under vacuum (500-600 mm Hg) to ⅖ths volume Hexanes (2.86 L) were added the mixture was stirred at 25-30° C. for 1 hour The solid was filtered washed with hexanes (1.43 L) dried at 45-50° C. under vacuum (500-600 mm Hg)

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Isopropyl-5-methylaniline (286 g, 1.91 mol) and sodium bicarbonate (270 g, 3.22 mol) were charged in to a round bottomed flask with stirring under nitrogen atmosphere and cooled to 0-5° C. 2-Chloroacetyl chloride (218 g, 1.93 mol) was added drop wise at 0-5° C. over a period of 1 hour. The reaction was stirred at 0-5° C. for 1 hour. After completion of the reaction, purified water (2.86 L) was added and stirred at 25-30° C. for 15 minutes. The layers were then separated. The organic layer was washed with water (2×2.86 L) and with brine (1.43 L). The aqueous layers were combined and extracted with ethyl acetate (1.43 L). The organic layers were dried with sodium sulphate, filtered, and concentrated at 50-55° C. under vacuum (500-600 mm Hg) to 2/5ths volume. Hexanes (2.86 L) were added and the mixture was stirred at 25-30° C. for 1 hour. The solid was filtered, washed with hexanes (1.43 L), and dried at 45-50° C. under vacuum (500-600 mm Hg) to give 2-chloro-N-(2-isopropyl-5-methylphenyl)acetamide as an off-white solid (270 g, 66%): mp 97-99° C.; 1H NMR (300 MHz, CDCl3) δ 8.27 (s, 1H), 7.60 (s, 1H), 7.20 (d, J=7.95 Hz, 1H), 7.04 (d, J=7.89 Hz, 1H), 4.25 (s, 2H), 2.99 (q, J=6.78 Hz, 1H), 2.34 (s, 3H), 1.26 (d, J=6.84 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 164.07, 137.28, 136.33, 132.95, 127.35, 125.62, 124.46, 43.21, 27.86, 22.98, 21.00; ESIMS m/z 226 ([M+H]+). The reaction was stirred at 0-5° C. for 1 hour After completion of the reaction purified water (2.86 L) was added stirred at 25-30° C. for 15 minutes The layers were then separated The organic layer was washed with water (2×2.86 L) and with brine (1.43 L) extracted with ethyl acetate (1.43 L) The organic layers were dried with sodium sulphate filtered concentrated at 50-55° C. under vacuum (500-600 mm Hg) to 2/5ths volume Hexanes (2.86 L) were added the mixture was stirred at 25-30° C. for 1 hour The solid was filtered washed with hexanes (1.43 L) dried at 45-50° C. under vacuum (500-600 mm Hg)

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 2-isopropyl-5-methylaniline (1.0 g, 6.7 mmol) in a 25 mL vial equipped with a stir bar, Vigreux column, and nitrogen was added carbon disulfide (3.0 mL, 50 mmol). The reaction was heated to 40° C. and cooled immediately. To this solution was added triethylamine (0.93 mL, 6.7 mmol). The reaction was heated to 50° C. for 90 minutes and cooled to room temperature overnight. The reaction mixture was transferred to a 100 mL round-bottomed flask and concentrated. The residue was taken up in acetonitrile (33.5 mL) and treated with N,N′-diisopropycarbodiimide (1.04 mL, 6.70 mmol). The reaction was stopped after a few h and concentrated. Purification by flash column chromatography using 2.5-5% ethyl acetate/hexanes as eluent provided a mixture of products. Re-purification by reversed phase column chromatography using 5-100% acetonitrile/water as eluent provided the title compound (65% in dichloromethane, 0.62 g, 31%), which was used without further purification: IR (thin film) 2963 (m), 2924 (m), 2869 (w), 2089 (vs), 1611 (w), 1501 (m) cm−1; 1H NMR (300 MHz, CDCl3) δ 7.16 (d, J=8.6 Hz, 1H), 7.09-7.03 (m, 2H), 3.19 (h, J=6.8 Hz, 1H), 2.30 (s, 3H), 1.24 (d, J=6.9 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 141.50, 136.70, 134.59, 128.84, 128.58, 127.12, 126.05, 29.20, 22.83, 20.62. cooled immediately The reaction was heated to 50° C. for 90 minutes cooled to room temperature overnight The reaction mixture was transferred to a 100 mL round-bottomed flask concentrated concentrated Purification by flash column chromatography provided a mixture of products

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 4-methyl-2-nitro-1-(prop-1-en-2-yl)benzene (0.986 g, 5.56 mmol) in a 100 mL round-bottomed flask equipped with a stir bar was added ethyl acetate (55.6 mL) and palladium on carbon (1.18 g, 0.556 mmol). The reaction was evacuated and backfilled with hydrogen (balloon). The reaction was stirred under an atmosphere of hydrogen overnight. The reaction mixture was filtered through a pad of Celite® and concentrated providing the title compound as a clear and colorless oil (0.788 g, 95%): IR (thin film) 3464 (m), 3372 (m), 3011 (m), 2959 (s), 2869 (m), 1621 (m), 1575 (m), 1509 (m) cm−1; 1H NMR (400 MHz, CDCl3) δ 7.03 (d, J=7.8 Hz, 1H), 6.61 (dd, J=7.8, 1.7 Hz, 1H), 6.54-6.50 (m, 1H), 3.59 (bs, 2H), 2.87 (hept, J=6.8 Hz, 1H), 2.24 (s, 3H), 1.24 (d, J=6.8 Hz, 6H); 13C NMR (101 MHz, CDCl3) δ 143.14, 136.16, 129.82, 125.33, 119.79, 116.55, 99.97, 27.36, 22.41, 20.96. The reaction was evacuated The reaction mixture was filtered through a pad of Celite® concentrated