Sulfuric Acid → HCID 22161962, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-hydroxy-2,3-dihydrobenzothiophene (500 mg, 3.28 mmoles) in 20 mL benzene in a sealable tube was added t-butanol (729 mg, 9.84 mmoles, 3.0 eq) and 0.4 mL concentrated H2SO4. The tube was sealed and the reaction mixture heated at 60° C. for 24 hours. The reaction mixture was cooled, diluted with water (50 mL) and extracted 2×25 mL ether. The combined extracts were washed with sodium bicarbonate (1×25 mL), H2O (1×25 mL) and brine (1×25 mL). The organic layer was then dried over Na2SO4, filtered and concentrated to give 220 mg crude product. Purification by flash chromatography (90/10, hexane/EtOAc) afforded 125 mg pure product (18%) mp 90°-93° C.

Provenance & Evidence