Sodium Iodide → 2-(2-(4-Fluorobenzyl)thiophen-3-yl)ethanol

Temperature

0 °C

Chlorotrimethylsilane (5.56 g, 51.2 mmol) was added slowly to a solution of sodium iodide (7.7 g, 51.2 mmol) in acetonitrile (80 mL) at rt. After stirring for 15 min the mixture was cooled to 0° C. and a solution of (3-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)(4-fluorophenyl)methanol (3.75 g, 10.2 mmol) in acetonitrile (10 mL) was added dropwise. The resulting mixture was stirred at 0° C. for 1 h and then at rt for 2 h. After cooling down to 0° C., 2 N sodium hydroxide (30 mL) was added slowly and the mixture stirred for 30 min. 100 mL of water was added and the mixture was extracted with ethyl acetate (3×80 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo and the product purified by flash chromatography eluting with ethyl acetate/hexane (1:20) to afford the title compound as a solid (1.8 g, 75%). MS (M+H)+ 237.

1. stirringThe resulting mixture was stirred at 0° C. for 1 h
2. waitat rt for 2 h
3. temperatureAfter cooling down to 0° C.
4. stirringthe mixture stirred for 30 min
5. extractionthe mixture was extracted with ethyl acetate (3×80 mL)
6. washThe combined organic layers were washed with brine (100 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. customThe solvent was evaporated in vacuo
10. customthe product purified by flash chromatography
11. washeluting with ethyl acetate/hexane (1:20)

ORD record

ord-ee15e185012c460283c1d7f8de5de45c

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786132B2