Diethyl Ether → 4,4-Dimethyl-5-methoxypent-1-ene

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Reaction Steps

2,2-Dimethylpent-4-en-1-ol (4.0 g.) was added dropwise to a suspension of sodium hydride (1.13 g. 80% dispersion in oil, washed with hexane) in dry dimethylformamide (80 ml.) under nitrogen. After stirring for 1 hour, iodomethane (5.3 g.) was added dropwise and the mixture stirred for a further hour. Diethyl ether (100 ml.) was added and was followed by slow addition of water (100 ml.). The ethereal extracts were evaporated in vacuo and the residue was dissolved in hexane (50 ml.). The hexane solution was washed with water and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo and 4,4-dimethyl-5-methoxypent-1-ene was obtained as a colourless oil (1.9 g.).

Provenance & Evidence