4-Toluenesulfonyl chloride → (2,3-Dihydro-1-benzofuran-2-yl)methyl 4-methylbenzene-1-sulfonate

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Reaction Steps

p-Toluenesulphonyl chloride (26.7 g, 140 mmol) was added to a solution of (2,3-dihydro-benzofuran-2-yl)-methanol (preparation 96) (21 g, 140 mmol) in pyridine (400 mL) and the mixture was stirred at room temperature for 4 days. The reaction mixture was then concentrated in vacuo and the residue was azeotroped with toluene, diluted with ethyl acetate (500 mL) and washed with 2M hydrochloric acid (2×300 mL). The organic solution was dried over magnesium sulfate and concentrated in vacuo to give a brown oil. Trituration of the oil in cyclohexane then afforded the title compound as a white solid in 79% yield, 33.5 g. LRMS APCI m/z 305 [M+H]+

Provenance & Evidence