HCID 12931926, compound → HCID 13719999, compound

Participants

Reaction Steps

A solution of 4,8-dimethyl-7-nonen-2-yn-4-ol (7.78 g; 44.5 mmol) in dry THF (300 ml) was cooled into an ice-water bath, with stirring under nitrogen. Solid LiAlH4 (2.15 g; 53.8 mmol) was added all at once. After 5 minutes, the cooling bath is removed and the reaction is stirred for one hour, then refluxed for 4 hours. After cooling into an ice-water bath, the reaction was treated cautiously with water (2.2 mml), 5% aq. NaOH (6.6 ml) and water (2.2 ml). The reaction was warmed up to room temperature and stirred until a white slurry was observed. Solid anhydrous sodium sulfate (ca 20 g) was added to the mixture in order to dry the medium. The solid was filtered off, thoroughly rinsed with diethyl ether. The filtrate was concentrated in vacuo. The product was purified by column chromatography on silica gel (eluting with heptanes/ethyl acetate 3:1) followed by bulb-to-bulb distillation (75° C./1.2 mbar). The product was obtained as a liquid (3.8 g; 94% pure by GC; 21.3 mmol; yield: 48%).

Provenance & Evidence