1-cyclohexylprop-2-en-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 140 ml of dry tetrahydrofuran, degassed and flushed with nitrogen (3×) and cooled to 0° C. under nitrogen, was added 1.3M vinyl magnesium bromide (195 ml, 253.5 mmol) in tetrahydrofuran rapidly and dropwise over 5 minutes. The resulting solution was stirred for 5 minutes at 0° C. under nitrogen after which a solution of 24.0 g (223 mmol) of cyclohexylcarboxaldehyde in 40 ml of dry tetrahydrofuran was added via syringe at 0° C. The resulting mixture was stirred for 3.75 hours at 0° to 5° C. under a nitrogen atmosphere after which the reaction was quenched at 0° C. by careful addition of saturated aqueous ammonium chloride. The resulting suspension was poured into 1 L of ice cold, saturated, aqueous ammonium chloride and extracted with three 600 ml portions of ethyl acetate. The ethyl acetate extracts were combined and washed with 1 L of saturated aqueous ammonium chloride, 1 L of saturated aqueous sodium bicarbonate, then twice with 1 L each of brine. The ethyl acetate extract was dried thoroughly over magnesium sulfate, filtered, and concentrated at room temperature via rotovap to give 31.0 g of 1-cyclohexylprop-2-enol. To 140 ml of dry tetrahydrofuran, degassed flushed with nitrogen (3×) was added via syringe at 0° C was quenched at 0° C. by careful addition of saturated aqueous ammonium chloride The resulting suspension was poured into 1 L of ice cold saturated, aqueous ammonium chloride and extracted with three 600 ml portions of ethyl acetate washed with 1 L of saturated aqueous ammonium chloride, 1 L of saturated aqueous sodium bicarbonate The ethyl acetate extract was dried thoroughly over magnesium sulfate filtered concentrated at room temperature via rotovap

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 140 ml of dry tetrahydrofuran, degassed and flushed with nitrogen (3×) and cooled to 0° C. under nitrogen, was added 1.3M vinyl magnesium bromide (195 ml, 253.5 mmol) in tetrahydrofuran rapidly and dropwise over 5 minutes. The resulting solution was stirred for 5 minutes at 0° C. under nitrogen after which a solution of 24.0 g (223 mmol) of cyclohexylcarboxaldehyde in 40 ml of dry tetrahydrofuran was added via syringe at 0° C. The resulting mixture was stirred for 3.75 hours at 0° to 5° C. under a nitrogen atmosphere after which the reaction was quenched at 0° C. by careful addition of saturated aqueous ammonium chloride. The resulting suspension was poured into 1 L of ice cold, saturated, aqueous ammonium chloride and extracted with three 600 ml portions of ethyl acetate. The ethyl acetate extracts were combined and washed with 1 L of saturated aqueous ammonium chloride, 1 L of saturated aqueous sodium bicarbonate, then twice with 1 L each of brine. The ethyl acetate extract was dried thoroughly over magnesium sulfate, filtered, and concentrated at room temperature via rotovap to give 31.0 g of 1-cyclohexylprop-2-enol. To 140 ml of dry tetrahydrofuran, degassed flushed with nitrogen (3×) was added via syringe at 0° C was quenched at 0° C. by careful addition of saturated aqueous ammonium chloride The resulting suspension was poured into 1 L of ice cold saturated, aqueous ammonium chloride and extracted with three 600 ml portions of ethyl acetate washed with 1 L of saturated aqueous ammonium chloride, 1 L of saturated aqueous sodium bicarbonate The ethyl acetate extract was dried thoroughly over magnesium sulfate filtered concentrated at room temperature via rotovap

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of Example 36A (5.62 g, 40.1 mmol) and 1,5-hexadiene (3.56 mL, 30.1 mmol) in 1,2-dichloroethane (70 mL), stirring at 0° C., was added thionyl bromide (4.66 mL, 60.12 mmol). The reaction was stirred for 2 hours at 0° C. and then quenched with water. The mixture was extracted with diethyl ether and the diethyl ether layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.46 g, 43%). 1H NMR (300 MHz, CDCl3): δ ppm 1.16 (m, 6 H) 1.69 (m, 4 H) 1.98 (m, 1 H) 3.94 (m, 2 H) 5.65 (m, 2 H). quenched with water The mixture was extracted with diethyl ether the diethyl ether layer was washed with saturated sodium bicarbonate solution dried with sodium sulfate filtered concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of Example 36A (5.62 g, 40.1 mmol) and 1,5-hexadiene (3.56 mL, 30.1 mmol) in 1,2-dichloroethane (70 mL), stirring at 0° C., was added thionyl bromide (4.66 mL, 60.12 mmol). The reaction was stirred for 2 hours at 0° C. and then quenched with water. The mixture was extracted with diethyl ether and the diethyl ether layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.46 g, 43%). 1H NMR (300 MHz, CDCl3): δ ppm 1.16 (m, 6 H) 1.69 (m, 4 H) 1.98 (m, 1 H) 3.94 (m, 2 H) 5.65 (m, 2 H). quenched with water The mixture was extracted with diethyl ether the diethyl ether layer was washed with saturated sodium bicarbonate solution dried with sodium sulfate filtered concentrated in vacuo

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of cyclohexanecarbaldehyde (4.79 mL, 39.8 mmol) in tetrahydrofuran (30 mL) was added dropwise to a solution of vinylmagnesium bromide (47.8 mL, 1 M in tetrahydrofuran, 47.8 mmol) stirring at −20° C. The solution was stirred for 30 minutes at −20° C. at which time saturated ammonium chloride solution (75 mL) was added and the reaction was allowed to warm to 25° C. The solution was diluted with water and extracted three times with ethyl acetate. The ethyl acetate layers were combined and washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane, followed by 5% and 10% ethyl acetate in hexane to give the title compound (2.11 g, 38%). 1H NMR (300 MHz, CDCl3): δ ppm 1.40 (m, 11 H) 3.85 (m, 1H) 5.17 (m, 2 H) 5.86 (m, 1 H). was added to warm to 25° C extracted three times with ethyl acetate washed with brine dried with sodium sulfate filtered concentrated in vacuo The residue was chromatographed on silica gel eluting with hexane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 140 ml of dry tetrahydrofuran, degassed and flushed with nitrogen (3×) and cooled to 0° C. under nitrogen, was added 1.3M vinyl magnesium bromide (195 ml, 253.5 mmol) in tetrahydrofuran rapidly and dropwise over 5 minutes. The resulting solution was stirred for 5 minutes at 0° C. under nitrogen after which a solution of 24.0 g (223 mmol) of cyclohexylcarboxaldehyde in 40 ml of dry tetrahydrofuran was added via syringe at 0° C. The resulting mixture was stirred for 3.75 hours at 0° to 5° C. under a nitrogen atmosphere after which the reaction was quenched at 0° C. by careful addition of saturated aqueous ammonium chloride. The resulting suspension was poured into 1 L of ice cold, saturated, aqueous ammonium chloride and extracted with ethyl acetate. The ethyl acetate extracts were combined and washed with saturated aqueous ammonium chloride, saturated aqueous sodium bicarbonate, then with brine. The ethyl acetate extract was dried over magnesium sulfate, filtered, and concentrated at room temperature to give 31.0 g of 1-cyclohexyl-prop-2-enol. To 140 ml of dry tetrahydrofuran, degassed flushed with nitrogen (3×) was added via syringe at 0° C was quenched at 0° C. by careful addition of saturated aqueous ammonium chloride The resulting suspension was poured into 1 L of ice cold saturated, aqueous ammonium chloride and extracted with ethyl acetate washed with saturated aqueous ammonium chloride, saturated aqueous sodium bicarbonate The ethyl acetate extract was dried over magnesium sulfate filtered concentrated at room temperature

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of Example 36A (5.62 g, 40.1 mmol) and 1,5-hexadiene (3.56 mL, 30.1 mmol) in 1,2-dichloroethane (70 mL), stirring at 0° C., was added thionyl bromide (4.66 mL, 60.12 mmol). The reaction was stirred for 2 hours at 0° C. and then quenched with water. The mixture was extracted with diethyl ether and the diethyl ether layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.46 g, 43%). 1H NMR (300 MHz, CDCl3): δ ppm 1.16 (m, 6 H) 1.69 (m, 4 H) 1.98 (m, 1 H) 3.94 (m, 2 H) 5.65 (m, 2 H). quenched with water The mixture was extracted with diethyl ether the diethyl ether layer was washed with saturated sodium bicarbonate solution dried with sodium sulfate filtered concentrated in vacuo

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of cyclohexanecarbaldehyde (4.79 mL, 39.8 mmol) in tetrahydrofuran (30 mL) was added dropwise to a solution of vinylmagnesium bromide (47.8 mL, 1 M in tetrahydrofuran, 47.8 mmol) stirring at −20° C. The solution was stirred for 30 minutes at −20° C. at which time saturated ammonium chloride solution (75 mL) was added and the reaction was allowed to warm to 25° C. The solution was diluted with water and extracted three times with ethyl acetate. The ethyl acetate layers were combined and washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane, followed by 5% and 10% ethyl acetate in hexane to give the title compound (2.11 g, 38%). 1H NMR (300 MHz, CDCl3): δ ppm 1.40 (m, 11 H) 3.85 (m, 1H) 5.17 (m, 2 H) 5.86 (m, 1 H). was added to warm to 25° C extracted three times with ethyl acetate washed with brine dried with sodium sulfate filtered concentrated in vacuo The residue was chromatographed on silica gel eluting with hexane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of Example 36A (5.62 g, 40.1 mmol) and 1,5-hexadiene (3.56 mL, 30.1 mmol) in 1,2-dichloroethane (70 mL), stirring at 0° C., was added thionyl bromide (4.66 mL, 60.12 mmol). The reaction was stirred for 2 hours at 0° C. and then quenched with water. The mixture was extracted with diethyl ether and the diethyl ether layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.46 g, 43%). 1H NMR (300 MHz, CDCl3): δ ppm 1.16 m, 6 H) 1.69 m, 4 H) 1.98 m, 1 H) 3.94 m, 2 H) 5.65 m, 2 H). quenched with water The mixture was extracted with diethyl ether the diethyl ether layer was washed with saturated sodium bicarbonate solution dried with sodium sulfate filtered concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of Example 36A (5.62 g, 40.1 mmol) and 1,5-hexadiene (3.56 mL, 30.1 mmol) in 1,2-dichloroethane (70 mL), stirring at 0° C., was added thionyl bromide (4.66 mL, 60.12 mmol). The reaction was stirred for 2 hours at 0° C. and then quenched with water. The mixture was extracted with diethyl ether and the diethyl ether layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.46 g, 43%). 1H NMR (300 MHz, CDCl3): δ ppm 1.16 m, 6 H) 1.69 m, 4 H) 1.98 m, 1 H) 3.94 m, 2 H) 5.65 m, 2 H). quenched with water The mixture was extracted with diethyl ether the diethyl ether layer was washed with saturated sodium bicarbonate solution dried with sodium sulfate filtered concentrated in vacuo