Hydrochloric Acid → HCID 86753103, compound

Participants

Reaction Steps

To a solution of enone 4 (150 g, 392 mmol), cerium trichloride heptahydrate (152 g, 408 mmol), methanol (500 mL), and CH2Cl2 (1.5 L) at 0° C. was added NaBH4 (14.4 g) in 0.2 g portions over 1 h. After stirring for 2 h, the reaction was poured into 1M HCl (500 mL), the layers were separated, the aqueous layer was extracted with CH2 Cl2 (2×300 mL), and the combined organic layers were dried over MgSO4, filtered, and concentrated to provide 150.4 g (100%) of a 1:1 mixture of the two diastereomeric allylic alcohols. Separation of 200 g of the mixture (from several combined reactions) by HPLC (40% ethyl acetate in hexane) afforded 23.7 g (12%) of alcohol 42.

Provenance & Evidence