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

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.).

1. stirringthe mixture stirred for a further hour
2. customThe ethereal extracts were evaporated in vacuo
3. dissolutionthe residue was dissolved in hexane (50 ml.)
4. washThe hexane solution was washed with water
5. dry with materialdried over anhydrous magnesium sulphate
6. customThe solvent was removed in vacuo

ORD record

ord-f40669316c4f49a29a969bcddc3e9369

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05502073