2-Thiophenecarboxaldehyde → 1-(Thiophen-2-yl)propan-1-ol

Temperature

23 °C

A 1.0M solution of ethylmagnesium bromide in THF (100 mL) is cooled to -78° C. and 2-thiophene carboxaldehyde (9.35 mL) is added. The reaction is allowed to warm to 23° C. for 1 h, then recooled to -78° C. and quenched with saturated ammonium chloride. After allowing to warm to 23° C., the reaction is extracted with ether (800 mL) and the ethereal layer is washed with water (2×150 mL) and brine. The organic phase is dried over MgSO4, filtered and concentrated in vacuo. The product is purified by chromatography over silica gel(2 kg), eluting with 30% ether in pentane to give 13.4 g of the title product as a colorless oil.

1. customrecooled to -78° C.
2. customquenched with saturated ammonium chloride
3. temperatureto warm to 23° C.
4. extractionthe reaction is extracted with ether (800 mL)
5. washthe ethereal layer is washed with water (2×150 mL) and brine
6. dry with materialThe organic phase is dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe product is purified by chromatography over silica gel(2 kg)
10. washeluting with 30% ether in pentane

ORD record

ord-64cc80af7e504cf78534b73c9988dbf9

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05686486