Sodium Hydroxide → HCID 55288000, compound

Participants

Reaction Steps

(±)-(3-Hydroxy-5-methyl-hex-4-enyl)carbamic acid methyl ester (38.9 g, 219 mmol) dissolved in tetrahydrofuran (150 mL) was added drop-wise to a refluxing solution of LiAlH4 (1M in tetrahydrofuran, 232 mL) maintaining reflux. After refluxing for 2 h. the mixture was cooled on an ice bath and 15% aq. sodium hydroxide (50 mL) was added drop-wise until a white precipitate separated out. The precipitate was filtrated and washed with tetrahydrofuran (2×200 mL), dichloromethane (2×200 mL) and diethylether (2×200 mL). The combined washes were evaporated. The resulting oil was redissolved in diethylether, dried (sodium sulfate), filtered and evaporated to give the crude product (29.5 g, 100%) as a yellow oil. The crude product was used without further purification.

Provenance & Evidence