Potassium Carbonate → 6-Methoxy-1-benzothiophene

Participants

Reaction Steps

A mixture of 3-methoxybenzenethiol (10 ml, 11.30 g, 80 mmole), K2CO3 (11.15 g, 80 mmole) and bromoacetaldehyde diethyl acetal (12 ml, 15.72 g, 80 mmole) in acetone (100 ml) was stirred at ambient temperature for 16 hours, then filtered. The filtrate was subsequently concentrated, in vacuo. The residue obtained was partitioned between H2O (150 ml) and Et2O (150 ml). The layers were separated and the aqueous phase was extracted with Et2O (150 ml). The combined organic extracts were washed with 0.5 M KOH (aq), H2O and brine, then dried over Na2SO4 and concentrated, in vacuo, to give 20.4 g of an amber oil which was used directly in the subsequent cyclization without any further purification.

Provenance & Evidence