Ethanol → 2-(5-(2-Hydroxyethyl)thiophen-2-yl)acetic acid

A solution of 2-[5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-2-thienyl]acetonitrile (3.0 g, 10.7 mmol) in ethanol (30 mL) was added to a stirred solution of potassium hydroxide (1.2 g, 21.4 mmol) in water (30 mL). The resultant mixture was stirred at 100° C. for 4 h. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate (30 mL) and brine (30 mL). The aqueous layer was cooled with ice and acidified with concentrated HCl until pH 1 was reached. The aqueous solution was then extracted with ethyl acetate (3×30 mL). The combine organic phases were washed with brine (30 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound as a yellow solid (1.35 g, 68%) which was used in the next step without further purification.

1. concentrationThe reaction mixture was concentrated in vacuo
2. customthe residue partitioned between ethyl acetate (30 mL) and brine (30 mL)
3. temperatureThe aqueous layer was cooled with ice
4. extractionThe aqueous solution was then extracted with ethyl acetate (3×30 mL)
5. washThe combine organic phases were washed with brine (30 mL)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-7b87c461562d4bb8a8d8758e67299637

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133185B2