Hydrochloric Acid → 2-[5-(Hydroxymethyl)-2-thienyl]acetic acid

To a solution of methyl 2-[5-(hydroxymethyl)-2-thienyl]acetate in tetrahydrofuran (10 mL) and methanol (10 mL) was added 1 N aqueous solution of lithium hydroxide (11.83 mL) and the resulting solution was stirred at room temperature for 4 h. The reaction mixture was cooled to 0° C. and acidified to pH 1 with 2 N aqueous solution of HCl. The solution was concentrated in vacuo and the residue partitioned between ethyl acetate (30 mL) and water (30 mL). The organic phases were dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound as an orange solid (1.02 g, quantitative yield) which was used in the next step without further purification.

1. temperatureThe reaction mixture was cooled to 0° C.
2. concentrationThe solution was concentrated in vacuo
3. customthe residue partitioned between ethyl acetate (30 mL) and water (30 mL)
4. dry with materialThe organic phases were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-b96ccffbaeeb4ef8898c09f10211e455

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133185B2