HCID 15023219, compound → HCID 14890667, compound

Participants

Reaction Conditions

Reaction Steps

The acyl chloride prepared in Step A was dissolved in 40 mL of tetrahydrofuran and was chilled to -78° C. under an inert atmosphere. To this pale greenish solution at -78° C. was added 10 mL lithium aluminum hydride in tetrahydrofuran solution (1 M, 10 mmol). Reduction was allowed to proceed at -78° C. for 20 minutes before it was diluted with H2SO4 dilute solution (2 M, 20 mL). The desired product was extracted twice into ethyl acetate (40 mL×2). Organic layers were combined, dried over MgSO4 and concentrated under reduced pressure to give 2.64 g (69.4%) of the title compound. The crude allylic alcohol was used in the next step without further purification. An analytically pure sample was prepared by crystallization from a mixture of ethyl acetate-hexanes (1:9, v/v) m.p.=110°-112° C.

Provenance & Evidence