Methanol → HCID 23349109, compound

Participants

Reaction Steps

(E,E,E,E)-3,7-dimethyl-9-(2,4-dimethyl-3-furyl)-2,4,6,8-nonatetraenoic acid ethyl ester (6 g.) in ether (25 ml.) was added to a solution of diisobutyl aluminum hydride (38 ml.; 25% by volume in hexane) at -40° and stirred for 30 minutes at room temperature. Aqueous methanol (1:1 parts by volume; 1.6 ml.) was added. The mixture was then carefully warmed to room temperature and then treated with anhydrous magnesium sulfate. The solids were filtered off and the solvents were removed to give (E,E,E,E)-3,7-dimethyl-9-(2,4,-dimethyl-3-furyl)-2,4,6,8-nonatetraenol as an oil. The pmr spectrum showed the complete absence of ester or aldehyde functions.

Provenance & Evidence