7-Methoxybenzo[b]thiophene → HCID 22171216, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-benzothien-7-yl methyl ether (230 mg, 1.40 mmol) in dry THF (5 ML) was added dropwise to a freshly prepared solution of 2,2,6,6 tetramethyl-lithio-piperidine (1.68 mmol) in THF (10 mL) at −78° C. The resulting solution was stirred at this temperature for 30 mins before perchloryl fluoride gas was condensed into the reaction. After the strong exotherm had stopped the mixture was allowed to stir at −78° C. for a further 30 mins. After this time the reaction was quenched with NH4Cl (sat, 20 mL) and diluted with diethyl ether. The organic phase was dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography eluting silica gel with hexane to yield a colourless oil (128 mg, 50%); δH (300 MHz, CDCl3) 7.32-7.20 (2H, m, Ar), 6.80-6.62 (2H, m, Ar), 3.95 (3H, s, OCH3).

Provenance & Evidence