反应详情

Borane (1M in THF, 6.11 mL, 6.11 mmol) was added to a stirred suspension of 3-chloro-1-benzothiophene-2-carboxylic acid (1.00 g, 4.70 mmol) in dry THF (2 mL) at 0° C. under N2. The reaction was allowed to warm to room temperature and was heated at reflux for 1½ h. The reaction was quenched with water (5 mL) and saturated K2CO3 (10 mL), then extracted with EtOAc (3×30 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford (3-chloro-1-benzothien-2-yl)methanol. 1H NMR (500 MHz, CDCl3): δ 7.79-7.77 (m, 2H); 7.45-7.42 (m, 1H); 7.39-7.36 (m, 1H); 4.96 (s, 2H); 2.48 (s, 1H).

1. temperaturewas heated
2. temperatureat reflux for 1½ h
3. customThe reaction was quenched with water (5 mL) and saturated K2CO3 (10 mL)
4. extractionextracted with EtOAc (3×30 mL)
5. dry with materialThe combined extracts were dried (MgSO4)
6. concentrationconcentrated in vacuo