Toluene → HCID 86618041, compound

Participants

Reaction Steps

1M toluene solution (1.76 ml, 1.76 mmol) of diisobutylaluminum hydride was added dropwise to a toluene (6 ml) solution of methyl-(2E,5E,7S,8S)-3,7-dimethyl-8-[(triethylsilyl)oxy]deca-2,5-dienoate (0.22 g, 0.64 mmol) at −78° C. and the reaction solution was stirred at the same temperature for 30 minutes. The reaction solution was diluted with diethyl ether, followed by addition of a saturated potassium sodium tartrate tetrahydrate aqueous solution (1.0 ml) and was warmed to room temperature and stirred for two hours. After the organic layer was dried over anhydrous sodium sulfate and the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Merck, commercial name Silica Gel 60, 230-400 mesh; hexane:diethyl ether=8:1) to obtain the title compound (150 mg) as a colorless oil.

Provenance & Evidence