Hydrochloric Acid → HCID 58381713, compound

Participants

Reaction Conditions

Reaction Steps

LiAlH4 (2.05 g, 54.1 mmol) was suspended in dry diethyl ether (100 mL) at 0° C. under inert atmosphere. To this suspension was added dropwise a solution of S-(3Z,6Z,9Z,12Z)-pentadeca-3,6,9,12-tetraenyl ethanethioate (13.7 g, 49.2 mmol) in dry diethyl ether (50 mL) and the resulting grey mixture was stirred at 0° C. for ten minutes and then at ambient temperature for 30 minutes. The mixture was cooled to ˜5° C., added 1M HCl until pH=2 and filtrated through a short pad of celite. The pad was washed with water and diethyl ether, the phases were separated and the aqueous phase was extracted twice with diethyl ether (100 mL each). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to afford 7.8 g (67% yield) of the title compound as oil.

Provenance & Evidence