cyclopent-3-en-1-ylmethanol

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

Procedure: A mixture of (cyclopent-3-en-1-yl)methanol (1.96 g, 20 mmol) and para-toluenesulfonylchloride (3.81 g, 20 mmol) were stirred at room temperature for 2 hrs in pyridine (30 ml). After the concentration of pyridine, the reaction residues were extracted with dichloromethane, washed 1N HCl, dried with MgSO4, concentrated and separated by the column chromatography to give the desirable product (4.20 g). After the concentration of pyridine, the reaction residues were extracted with dichloromethane washed 1N HCl dried with MgSO4 concentrated separated by the column chromatography

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

Procedure: A mixture of (cyclopent-3-en-1-yl)methanol (1.96 g, 20 mmol) and para-toluenesulfonylchloride (3.81 g, 20 mmol) were stirred at room temperature for 2 hrs in pyridine (30 ml). After the concentration of pyridine, the reaction residues were extracted with dichloromethane, washed 1N HCl, dried with MgSO4, concentrated and separated by the column chromatography to give the desirable product (4.20 g). After the concentration of pyridine, the reaction residues were extracted with dichloromethane washed 1N HCl dried with MgSO4 concentrated separated by the column chromatography

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

Procedure: 4-Nitrobenzoyl chloride (3.46 g, 18.7 mmol) was added to a dichloromethane solution (34 mL) of cyclopent-3-en-1-ylmethanol (1.67 g, 17.0 mmol) and triethylamine (3.55 mL, 25.4 mmol). The solution was stirred at room temperature for 15 minutes. Saturated aqueous sodium bicarbonate solution was added, and the solution was extracted with dichloromethane. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Biotage 40M), eluting with 0-100% ethyl acetate/hexanes to give the title compound as a white solid. 1H NMR (500 MHz, CHCl3) δ 2.21 (dd, J=4.9, 14.8 Hz, 2H), 2.57 (dd, J=8.6, 15.1 Hz, 2H), 2.71-2.82 (m, 1H), 4.28 (d, J=7.2 Hz, 2H), 5.69 (s, 2H), 8.19 (d, J=8.6 Hz, 2H), 8.27 (d, J=8.6 Hz, 2H). the solution was extracted with dichloromethane The combined organic layers were dried (magnesium sulfate) filtered concentrated in vacuo The residue was purified by silica gel chromatography (Biotage 40M) eluting with 0-100% ethyl acetate/hexanes

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a flask under argon was placed cyclopent-3-enyl-methanol (7.86 g, 80 mmol) and pyridine (100 mL). To this mixture was slowly added benzoyl chloride (9.30 mL, 80 mmol). After addition was complete, the mixture was stirred at 25° C. for 1.5 h. After this time, the mixture was slowly treated with water (15 mL) and concentrated in vacuo to remove most of the pyridine. The mixture was taken up into chloroform (400 mL) and washed with water (300 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to afford benzoic acid cyclopent-3-enylmethyl ester (15.86 g, 98%) as a light yellow oil. In a flask under argon was placed After addition concentrated in vacuo to remove most of the pyridine washed with water (300 mL) The organic layer was separated dried over sodium sulfate filtered concentrated in vacuo

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

Procedure: 4-Nitrobenzoyl chloride (3.46 g, 18.7 mmol) was added to a dichloromethane solution (34 mL) of cyclopent-3-en-1-ylmethanol (1.67 g, 17.0 mmol) and triethylamine (3.55 mL, 25.4 mmol). The solution was stirred at room temperature for 15 minutes. Saturated aqueous sodium bicarbonate solution was added, and the solution was extracted with dichloromethane. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Biotage 40M), eluting with 0-100% ethyl acetate/hexanes to give the title compound as a white solid. 1H NMR (500 MHz, CHCl3) δ 2.21 (dd, J=4.9, 14.8 Hz, 2H), 2.57 (dd, J=8.6, 15.1 Hz, 2H), 2.71-2.82 (m, 1H), 4.28 (d, J=7.2 Hz, 2H), 5.69 (s, 2H), 8.19 (d, J=8.6 Hz, 2H), 8.27 (d, J=8.6 Hz, 2H). the solution was extracted with dichloromethane The combined organic layers were dried (magnesium sulfate) filtered concentrated in vacuo The residue was purified by silica gel chromatography (Biotage 40M) eluting with 0-100% ethyl acetate/hexanes

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a flask under argon was placed cyclopent-3-enyl-methanol (7.86 g, 80 mmol) and pyridine (100 mL). To this mixture was slowly added benzoyl chloride (9.30 mL, 80 mmol). After addition was complete, the mixture was stirred at 25° C. for 1.5 h. After this time, the mixture was slowly treated with water (15 mL) and concentrated in vacuo to remove most of the pyridine. The mixture was taken up into chloroform (400 mL) and washed with water (300 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to afford benzoic acid cyclopent-3-enylmethyl ester (15.86 g, 98%) as a light yellow oil. In a flask under argon was placed After addition concentrated in vacuo to remove most of the pyridine washed with water (300 mL) The organic layer was separated dried over sodium sulfate filtered concentrated in vacuo

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

Procedure: A solution of cyclopent-3-en-1-ylmethanol (3.50 g, 35.66 mmol) in anhydrous dimethylformamide (100 mL) at 0° C. was added sodium hydride (60% dispersion in mineral oil, 1.71 g, 42.79 mmol) portionwise under nitrogen. The mixture was stirred at 0° C. for 1 hour and then stirred at ambient temperature for 1 hour. para-Methoxybenzyl chloride (5.80 mL, 42.79 mmol) was added to the reaction mixture and the resulting mixture was stirred for 2 hours. The reaction mixture was quenched with methanol (10 mL) and then water (200 mL). The mixture was extracted with ethyl acetate and the organic layer was washed with saturated ammonium chloride (2×200 mL) and brine (200 mL); dried over anhydrous sodium sulfate; filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (3:1 hexanes:ethyl acetate) to provide the title compound (6.15 g, 79%): 1H NMR (300 MHz, CDCl3) δ 7.26 (d, J=8.8 Hz, 2H), 6.87 (d, J=8.8 Hz, 2H), 5.67-5.60 (m, 2H), 4.44 (s, 2H), 3.79 (s, 3H), 3.34 (d, J=7.2 Hz, 2H), 2.66-2.40 (m, 3H), 2.16-2.03 (m, 2H); MS (ES+) m/z 241.2 (M+23). stirred at ambient temperature for 1 hour the resulting mixture was stirred for 2 hours The reaction mixture was quenched with methanol (10 mL) The mixture was extracted with ethyl acetate the organic layer was washed with saturated ammonium chloride (2×200 mL) and brine (200 mL) dried over anhydrous sodium sulfate filtered concentrated in vacuo The residue was purified by silica gel column chromatography (3:1 hexanes:ethyl acetate)

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

Procedure: To a stirred, cooled (0° C.) solution of 4-hydroxymethylcyclopentene (J. -P. Depres and A. E. Green, J. Org. Chem. 1984, 49, 928-931, and references therein) (37.0 g, 276 mmol) in pyridine (450 mL) was added benzoylchloride (32.1 mL, 276 mmol) over 30 minutes. The resulting mixture was stirred at room temperature for 1.25 hours. Water (50 mL) was added and the volatiles removed in vacuo. The residual oil was dissolved in chloroform and the solution extracted with water and then dried over sodium sulfate. Evaporation of solvent gave (3-cyclopenten-1-yl)methylbenzoate as a yellow oil (53.94 g, 91%), sufficiently pure for use; 1H-NMR (DMSO-d6)δ: 7.98, 7.67, 7.56 (m, 5, C6H5), 5.72 (s, 2, CH=CH), 4.19 (m, 2, OCH2), 2.71 (m, 1, CH), 2.56-2.77 (m, overlapping solvent, 2CH), 2.21-2.14 (m, 2, 2CH). the volatiles removed in vacuo The residual oil was dissolved in chloroform the solution extracted with water dried over sodium sulfate Evaporation of solvent

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

Procedure: To a stirred, cooled (0° C.) solution of 4-hydroxymethylcyclopentene (J.-P. Depres and A. E. Green, J. Org. Chem. 1984, 49, 928-931, and references therein) (37.0 g, 276 mmol) in pyridine (450 mL) was added benzoylchloride (32.1 mL, 276 mmol) over 30 minutes. The resulting mixture was stirred at room temperature for 1.25 hours. Water (50 mL) was added and the volatiles removed in vacuo. The residual oil was dissolved in chloroform and the solution extracted with water and then dried over sodium sulfate. Evaporation of solvent gave (3-cyclopenten-1-yl)methylbenzoate as a yellow oil (53.94 g, 91%), sufficiently pure for use; 1H-NMR (DMSO-d6) δ: 7.98, 7.67, 7.56 (m, 5, C6H5), 5.72 (s, 2, CH=CH), 4.19 (m, 2, OCH2), 2.71 (m, 1, CH), 2.56-2.77 (m, overlapping solvent, 2CH), 2.21-2.14 (m, 2,2CH). the volatiles removed in vacuo The residual oil was dissolved in chloroform the solution extracted with water dried over sodium sulfate Evaporation of solvent

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

Procedure: To a stirred, cooled (0° C.) solution of 4-hydroxymethylcyclopentene (J.-P. Depres and A. E. Green, J. Org. Chem. 1984, 49, 928-931, and references therein) (37.0 g, 276 mmol) in pyridine (450 mL) was added benzoylchloride (32.1 mL, 276 mmol) over 30 minutes. The resulting mixture was stirred at room temperature for 1.25 hours. Water (50 mL) was added and the volatiles removed in vacuo. The residual oil was dissolved in chloroform and the solution extracted with water and then dried over sodium sulfate. Evaporation of solvent gave (3-cyclopenten-1-yl)methylbenzoate as a yellow oil (53.94 g, 91%), sufficiently pure for use; 1H-NMR (DMSO-d6) δ: 7.98, 7.67, 7.56 (m, 5, C6H5), 5.72 (s, 2, CH=CH), 4.19 (m, 2, OCH2), 2.71 (m, 1, CH), 2.56-2.77 (m, overlapping solvent, 2CH), 2.21-2.14 (mn, 2, 2CH). the volatiles removed in vacuo The residual oil was dissolved in chloroform the solution extracted with water dried over sodium sulfate Evaporation of solvent

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

Procedure: A mixture of (cyclopent-3-en-1-yl)methanol (1.96 g, 20 mmol) and para-toluenesulfonylchloride (3.81 g, 20 mmol) were stirred at room temperature for 2 hrs in pyridine (30 ml). After the concentration of pyridine, the reaction residues were extracted with dichloromethane, washed 1N HCl, dried with MgSO4, concentrated and separated by the column chromatography to give the desirable product (4.20 g). After the concentration of pyridine, the reaction residues were extracted with dichloromethane washed 1N HCl dried with MgSO4 concentrated separated by the column chromatography

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a flask under argon was placed cyclopent-3-enyl-methanol (7.86 g, 80 mmol) and pyridine (100 mL). To this mixture was slowly added benzoyl chloride (9.30 mL, 80 mmol). After addition was complete, the mixture was stirred at 25° C. for 1.5 h. After this time, the mixture was slowly treated with water (15 mL) and concentrated in vacuo to remove most of the pyridine. The mixture was taken up into chloroform (400 mL) and washed with water (300 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to afford benzoic acid cyclopent-3-enylmethyl ester (15.86 g, 98%) as a light yellow oil. In a flask under argon was placed After addition concentrated in vacuo to remove most of the pyridine washed with water (300 mL) The organic layer was separated dried over sodium sulfate filtered concentrated in vacuo