Hydrochloric Acid → HCID 57420145, compound

Participants

Reaction Steps

To a solution of the product from Step 3 (48 g, 157 mmol) in toluene (500 mL) cooled at −75° C. was added a solution of diisobutylaluminum hydride (1.0 M in toluene, 314 mL, 314 mmol) over a 45 min period. After additional 30 min at −75° C., the reaction mixture was poured into a ice-cold solution of 1 N hydrochloric acid (1.5 L) and the mixture was stirred at room temperature for 30 min. The product was extracted with ethyl acetate (2×500 mL) and organic extracts were washed with a saturated solution of sodium bicarbonate and brine. After removal of the solvent, the crude product was purified by chromatography on silica gel eluting with 7:1 hexane:ethyl acetate to give the title product as an oil.

Provenance & Evidence