(1-pentylcyclohexyl)methanol

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

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

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

Procedure: DMSO (930 L) was added to a −78° C. solution of oxalyl chloride (3.2 mL, 2 M/toluene) in CH2Cl2 (44 mL). After 15 min., a solution of alcohol 2-3 (968 mg, 5.3 mmol) in 14 mL CH2Cl2 was added by cannula, rinsing with 2 mL CH2Cl2. The reaction was stirred for 15 min. and Et3N (5.9 mL) was added. The reaction was allowed to warm to 0° C. and after 2 h, 100 mL saturated NaHCO3 solution was added. The resulting mixture was extracted with CH2Cl2 (3×) and the combined CH2Cl2 solution was washed with H2O and brine and then was dried (Na2SO4), filtered and evaporated to give the title compound. rinsing with 2 mL CH2Cl2 Et3N (5.9 mL) was added 100 mL saturated NaHCO3 solution was added The resulting mixture was extracted with CH2Cl2 (3×) the combined CH2Cl2 solution was washed with H2O and brine was dried (Na2SO4) filtered evaporated

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

Procedure: LiAlH4 (15 mL, 30 mmol, 2 M/THF) was added drop wise to a solution of 2-2 (1.773 g, 12.5 mmol) in ether (9 mL) at a rate to maintain a gentle reflux. The mixture was stirred further for 15 min. and then was cooled to 0° C. H2O (1 mL) was added followed by 3 M NaOH (1.2 mL) and more H2O (3 mL). The resulting mixture was allowed to warm to room temperature and after 1 h of stirring, 50 mL saturated NH4Cl solution was added. The mixture was extracted with dichloromethane (3×30 mL) and the combined dichloromethane solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. The residue was purified by flash chromatography using a combiflash system by Teledyne Isco (80 g silica gel, 0→100% ethyl acetate/hexanes) which gave the title compound (968 mg, 5.3 mmol, 42%). to maintain a gentle reflux to warm to room temperature and after 1 h of stirring The mixture was extracted with dichloromethane (3×30 mL) the combined dichloromethane solution was washed with brine was dried (Na2SO4) filtered evaporated The residue was purified by flash chromatography