Ammonia → 9-Mercapto-3-(2-(3-furyl)ethyl)-spiro[5.5]undecane

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Reaction Steps

A solution of 0.100 g of 9-acetylthio-3-(2-(3-furyl)ethyl)-spiro[5.5]undecane in 5 ml of methanol/tetrahydrofuran 3/1, was saturated with hydrogen and successively with gaseous ammonia and kept on standing for 3 hrs at room temperature. The mixture was evaporated to dryness and purified by flash chromatography (SiO2 ; n-hexane/diethylether 80/20) to give 0.080 g of 9-mercapto-3-(2-(3-furyl)ethyl)-spiro[5.5]undecane as a white sticky oil. TLC: Rf=0.38 (SiO2 plates, n-hexane/diethylether 80/20). 1H-NMR (300 MHz, CDCl3, ppm from TMS): 7.36 (1H, m), 7.20 (1H, m), 6.27 (1H, m), 2.90 (1H, m), 2.48 (2H, t), 1.90-0.85 (19H, m).

Provenance & Evidence