Methyl iodide → 4-Ethylsulfanyl-3-methoxy-3-methyl-but-1-yne

1-Ethylsulfanyl-2-methyl-but-3-yn-2-ol (0.29 g, 2.0 mmol) was added to a mixture of sodium hydride (60% dispersion in mineral oil, 88 mg, 2.2 mmol) in dimethylformamide (5 mL) under argon. Iodomethane (0.12 mL, 2.0 mmol) was then added to the reaction mixture via syringe and the mixture allowed to stir overnight. The mixture was poured onto water and extracted twice with diethyl ether. The diethyl ether extracts were washed with water and brine, dried over magnesium sulfate, filtered, and evaporated to yield a yellow oil. The oil was purified by column chromatography eluting with dichloromethane to yield the title compound as a clear liquid.

1. additionThe mixture was poured onto water
2. extractionextracted twice with diethyl ether
3. washThe diethyl ether extracts were washed with water and brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. customevaporated
7. customto yield a yellow oil
8. customThe oil was purified by column chromatography
9. washeluting with dichloromethane

ORD record

ord-420c1ea2d57844d8b5249066e8a96622

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765782B2