2,3-Dihydro-1lambda6-benzothiophene-1,1-dione → 2,3-Dihydrobenzo(b)thiophene

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Reaction Steps

A solution of 22.3 g (132 mmole) of the product of Part (ii) in 200 ml tetrahydrofuran was added dropwise with stirring to a mixture of 5.81 g (145 mmole) lithium aluminum hydride (95%) in 400 ml dry ethyl ether, at a rate sufficient to maintain gentle reflux. Refluxing was continued for 30 minutes. The mixture was cooled in ice and quenched by cautious addition of 6 ml water followed by 6 ml 15% (w/v) sodium hydroxide and 18 ml water. The resulting mixture was filtered, the organic phase washed with brine, dried (Na2SO4) and evaporated to provide a yellow oil which was distilled to yield 10.4 g (58%) product, b.p. 129°-131° C. The structure was verified by 1H-NMR spectroscopy.

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