HCID 57443971, compound → HCID 57443968, compound

Participants

Reaction Steps

To a solution of benzo[b]thiophene-2,6-dicarboxylic acid 2-ethyl ester (332 mg, 1.32 mmol) in 5 mL of anhydrous THF at 0 degrees Celsius was slowly added BH3. The resulting mixture was allowed to stir at 0 degrees Celsius for 30 mins and at rt overnight. After cooling to 0 degrees Celsius, the reaction mixture was quenched with 1N HCl. Additional 120 mL of water was added and THF was removed in vacuo. The solid was filtered and washed with water. After drying, 6-hydroxymethyl-benzo[b]thiophene-2-carboxylic acid ethyl ester was obtained as pale solid (229 mg, 73.2%). MS: calc'd 237 (MH+), exp 237 (MH+). 1H NMR (CDCl3, 400 MHz), 8.04 (s, 1H), 7.88 (s, 1H), 7.85 (d, 1H, J=8.4 Hz), 7.40 (d, 1H, J=8.0 Hz), 4.42 (q, 2H, J=7.2 Hz), 1.43 (t, 3H, J=7.2 Hz).

Provenance & Evidence