Acetic Acid → Methyl 2-[5-(hydroxymethyl)-2-thienyl]acetate

Temperature

0 °C

To a solution of methyl 2-(5-formyl-2-thienyl)acetate (3.88 g, 21.1 mmol) in methanol (4 mL) and tetrahydrofuran (16 mL) was added sodium borohydride (399 mg, 10.5 mmol) at −10° C. The reaction mixture was stirred at 0° C. for 1 h. Sodium borohydride (399 mg, 10.5 mmol) was added and the mixture left to stir at 0° C. for 2 h. Acetic acid (1.2 mL) was added and the reaction solution concentrated in vacuo. The residue was diluted with water (30 mL) and extracted with ethyl acetate (3×30 mL). The combined organic phases were washed with brine (20 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with 0-30% ethyl acetate in iso-hexane to give the title compound as a yellow oil (1.1 g, 28%).

1. waitthe mixture left
2. stirringto stir at 0° C. for 2 h
3. concentrationthe reaction solution concentrated in vacuo
4. additionThe residue was diluted with water (30 mL)
5. extractionextracted with ethyl acetate (3×30 mL)
6. washThe combined organic phases were washed with brine (20 mL)
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated in vacuo
9. customThe residue was purified by silica gel chromatography
10. washeluting with 0-30% ethyl acetate in iso-hexane

ORD record

ord-837191b93cd549efa46131324d3e962d

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133185B2