Hydrochloric Acid → 6-Methoxybenzo[b]thiophene-2-ethanol

Participants

Reaction Conditions

Reaction Steps

Butyllithium (2.5 M) (0.27 mol) was added dropwise to 6-methoxybenzo[b]-thiophene (0.25 mol) in tetrahydrofuran (1000 ml), stirred at −30° C. The mixture was stirred for 10 min at −30° C. Ethylene oxide (0.38 mol in 100 ml tetrahydrofuran) was added dropwise at −30° C. The mixture was allowed to warm to room temperature and stirred for 3 hours. The mixture was acidified with dilute HCl solution. The solvent was evaporated. The residue was diluted with water and this mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered and the solvent evaporated. The residue was stirred in hexane, filtered off and dried, yielding 41.3 g of 6-methoxybenzo[b]thiophene-2-ethanol (interm. 3).

Provenance & Evidence