Hydrochloric Acid → alpha-(3-Chloropropyl)-2-thiophenemethanol

Temperature

0 °C

4-Chloro-1-(2-thienyl)-1-butanone (9.37 g, 50 mmol) was dissolved in ethanol (100 ml) and the solution cooled to 0° C. Sodium borohydride (1.88 g, 50 mmol) was added in one portion and the reaction allowed to warm to room temperature, then stirred for 18 hours. Aqueous 2M hydrochloric acid was added dropwise until the reaction ceased to effervesce. The solvent was removed in vacuo and the residue partitioned between water and ethyl acetate. The layers were separated and the aqueous portion extracted with ethyl acetate (2×100 ml). The combined organic portions were washed with water (50 ml), dried (magnesium sulphate), filtered and evaporated. The residue was passed down a flash silica chromatography column, eluting with hexane: ethyl acetate (4:1) to afford the title compound as a pale straw coloured oil (7.58 g, 79%).

1. temperatureto warm to room temperature
2. customThe solvent was removed in vacuo
3. customthe residue partitioned between water and ethyl acetate
4. customThe layers were separated
5. extractionthe aqueous portion extracted with ethyl acetate (2×100 ml)
6. washThe combined organic portions were washed with water (50 ml)
7. dry with materialdried (magnesium sulphate)
8. filtrationfiltered
9. customevaporated
10. washeluting with hexane: ethyl acetate (4:1)

ORD record

ord-0e7b09ba79084a2fa6c77f1fe6042d27

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06743939B2