Sodium hydride → HCID 57989172, compound

Temperature

0 °C

A solution of 4-mercaptobutanol (4.936 g) in dry acetonitrile under argon was cooled to 0° C. and sodium hydride (60% in mineral oil, 2.044 g) was added portionwise. The mixture was stirred for 1 hour at 0° C. then 2-(2-bromoethyl)-1,3-dioxolane (9.26 g) was added and the resultant grey suspension was warmed to room temperature and stirred overnight. The reaction was quenched by addition of saturated aqueous sodium bicarbonate solution (150 mL) and then extracted with ethyl acetate (3×150 mL). The organics were combined and washed with brine (150 mL), dried over sodium sulfate, filtered and dried to afford the crude product. Purification was by silica gel chromatography eluting with 0-50% ethyl acetate in cyclohexane to afford the subtitled compound as a yellow oil. Yield 7.3 g.

1. temperaturethe resultant grey suspension was warmed to room temperature
2. stirringstirred overnight
3. customThe reaction was quenched by addition of saturated aqueous sodium bicarbonate solution (150 mL)
4. extractionextracted with ethyl acetate (3×150 mL)
5. washwashed with brine (150 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customdried
9. customto afford the crude product
10. customPurification
11. washeluting with 0-50% ethyl acetate in cyclohexane

ORD record

ord-71cdd28b525c40f58cb43351e6fb27e6

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2