Sodium hydride → 6-(2,2-Dimethoxyethylthio)hexan-1-ol

Temperature

0 °C

To a solution of 6-mercapto-hexan-1-ol (2.5 mL) in MeCN (30 mL) at 0° C. was added sodium hydride (60% suspension in mineral oil, 0.81 g). The mixture was stirred at 0° C. for 1 h then 2-bromo-1,1-dimethoxy-ethane (2.4 mL) was added. The resulting mixture was stirred at RT for 20 h, then was quenched by addition of saturated sodium bicarbonate solution. The mixture was extracted with ethyl acetate (×3), then the combined organics were washed with saturated sodium bicarbonate solution, then with brine, dried over sodium sulfate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with 25% ethyl acetate in cyclohexane to give the subtitled compound as a colourless liquid. Yield 1.85 g.

1. stirringThe resulting mixture was stirred at RT for 20 h
2. customwas quenched by addition of saturated sodium bicarbonate solution
3. extractionThe mixture was extracted with ethyl acetate (×3)
4. washthe combined organics were washed with saturated sodium bicarbonate solution
5. dry with materialwith brine, dried over sodium sulfate
6. filtrationfiltered
7. customevaporated in vacuo
8. customPurification
9. washeluting with 25% ethyl acetate in cyclohexane

ORD record

ord-6dd61b5dfc2e49398359dcc7affba2dc

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2