3-cyclopentylpropan-1-ol

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

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

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

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

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

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

Procedure: To a solution of 3-cyclopentyl-1-propanol (2.0 g, 15.6 mmol) in triethylamine (3.25 ml, 23.4 mmol) and dichloromethane (50 ml) was added 4-bromobenzenesulfonyl chloride (4.4 g, 17.6 mmol). The solution was stirred for 16 h, diluted with 2 N aqueous hydrochloric acid (100 ml) and extracted with dichloromethane (100 ml). The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) and brine (100 ml), dried (MgSO4) and concentrated in vacuo to give the title compound as a white crystalline solid (4.50 g, 80%). extracted with dichloromethane (100 ml) The extract was washed with saturated aqueous sodium hydrogen carbonate solution (100 ml) and brine (100 ml) dried (MgSO4) concentrated in vacuo

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

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

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To CH2Cl2 (100 mL) at −78° C. were added oxalyl chloride (4.1 mL, 46.8 mmol, Aldrich) and dry DMSO (5.5 mL, 78.0 mmol, Aldrich), dropwise. After 5 min, 3-cyclopentylpropan-1-ol (5.0 g, 39.0 mmol, Aldrich) in 5 mL of CH2Cl2 was added. The mixture was stirred for an additional 0.5 hr at −78° C., and triethylamine (27.2 mL, 195.0 mmol) was added. The mixture was then allowed to warm to room temperature over 0.5 hr. After stirring for 3 hr, 100 mL of water was added. The phases were separated, and the aqueous phase was extracted with diethyl ether (3×100 mL). The combined organic extracts were washed successively with 50 mL of aqueous 1% HCl, 50 mL of water, 50 mL of aqueous 5% NaHCO3 and 50 mL of saturated aqueous NaCl. The organic layer was dried (MgSO4), filtered and concentrated to provide 4.1 g (83%) of the title compound. MS (ESI+) m/z 144 (M+NH4)+. to warm to room temperature over 0.5 hr After stirring for 3 hr The phases were separated the aqueous phase was extracted with diethyl ether (3×100 mL) The combined organic extracts were washed successively with 50 mL of aqueous 1% HCl, 50 mL of water, 50 mL of aqueous 5% NaHCO3 and 50 mL of saturated aqueous NaCl The organic layer was dried (MgSO4) filtered concentrated

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To CH2Cl2 (100 mL) at −78° C. were added oxalyl chloride (4.1 mL, 46.8 mmol, Aldrich) and dry DMSO (5.5 mL, 78.0 mmol, Aldrich), dropwise. After 5 min, 3-cyclopentylpropan-1-ol (5.0 g, 39.0 mmol, Aldrich) in 5 mL of CH2Cl2 was added. The mixture was stirred for an additional 0.5 hr at −78° C., and triethylamine (27.2 mL, 195.0 mmol) was added. The mixture was then allowed to warm to room temperature over 0.5 hr. After stirring for 3 hr, 100 mL of water was added. The phases were separated, and the aqueous phase was extracted with diethyl ether (3×100 mL). The combined organic extracts were washed successively with 50 mL of aqueous 1% HCl, 50 mL of water, 50 mL of aqueous 5% NaHCO3 and 50 mL of saturated aqueous NaCl. The organic layer was dried (MgSO4), filtered and concentrated to provide 4.1 g (83%) of the title compound. MS (ESI+) m/z 144 (M+NH4)+. to warm to room temperature over 0.5 hr After stirring for 3 hr The phases were separated the aqueous phase was extracted with diethyl ether (3×100 mL) The combined organic extracts were washed successively with 50 mL of aqueous 1% HCl, 50 mL of water, 50 mL of aqueous 5% NaHCO3 and 50 mL of saturated aqueous NaCl The organic layer was dried (MgSO4) filtered concentrated

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

Procedure: 3-Cyclopentyl-1-propanol (15.0 g, 117 mmol) was dissolved in dichloromethane (600 mL) and treated with Celite (50 g) and pyridinium chlorochromate (50.0 g, 232 mmol). The reaction was stirred at room temperature for 24 hours. The reaction was found to be complete by thin layer chromatography (stain: potassium permanganate) and filtered through a pad of silica (dichloromethane) to afford 3-cyclopentyl-propionaldehyde as an oil (10.3 g, 70%). 1H NMR (CDCl3, 300 MHz) δ 11.1-10.8 (br s, 1H), 2.36 (t, 7.73 Hz, 2H), 1.8-1.5 (m, 9H), 1.09 (m, 2H). filtered through a pad of silica (dichloromethane)

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

Procedure: 3-Cyclopentyl-1-propanol (15.0 g, 117 mmol) was dissolved in dichloromethane (600 mL) and treated with Celite (50 g) and pyridinium chlorochromate (50.0 g, 232 mmol). The reaction was stirred at room temperature for 24 hours. The reaction was found to be complete by thin layer chromatography (stain: potassium permanganate) and filtered through a pad of silica (dichloromethane) to afford 3-cyclopentyl-propionaldehyde as an oil (10.3 g, 70%). 1H NMR (CDCl3, 300 MHz) δ 11.1-10.8 (br s, 1H), 2.36 (t, 7.73 Hz, 2H), 1.8-1.5 (m, 9H), 1.09 (m, 2H). filtered through a pad of silica (dichloromethane)