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-2fcc4dcec9bc43c6b9a7600c3822ba28

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858785B2