3-Chloro-1-benzothiophene-2-carboxylic acid → (3-Chloro-1-benzothien-2-yl)methanol

To an ice cold solution of 10.0 g (47.0 mmol) of 3-chloro-benzo[b]thiophene-2-carboxylic acid (11) in 200 mL of THF was added 47 mL of LiAlH4 (47 mmol, 1 M/THF). After 3 h, the reaction was quenched by addition of MeOH (ca. 40 mL). The volatiles were evaporated and the residue was treated with 50 mL 1 M HCl. After stirring for 10 min., the mixture was extracted with CH2Cl2 (3×150 mL). The combined CH2Cl2 solution was dried (MgSO4), filtered and evaporated. Purification by flash chromatography on silica gel (10-20% ethyl acetate/hexane) gave 4.32 g (21.6 mmol, 46%) of the alcohol (12).

1. customthe reaction was quenched by addition of MeOH (ca. 40 mL)
2. customThe volatiles were evaporated
3. additionthe residue was treated with 50 mL 1 M HCl
4. extractionthe mixture was extracted with CH2Cl2 (3×150 mL)
5. dry with materialThe combined CH2Cl2 solution was dried (MgSO4)
6. filtrationfiltered
7. customevaporated
8. customPurification by flash chromatography on silica gel (10-20% ethyl acetate/hexane)

ORD record

ord-cc73a821435b4775a26ed2b8022eaa18

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08754122B2