Sodium Hydroxide → 1318951-91-5

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence