Water → HCID 54333761, compound

Participants

Reaction Steps

A solution of 14.5 g of 5-chloro-6-methoxy-3,3-dimethyl-1-indanone, 13.3 ml of 3-buten-2-ol and 300 mg of p-toluenesulfonic acid in 150 ml of 2,2-dimethoxy-propane was boiled under reflux for 71 hours on a water separator filled with molecular sieve (0.4 nm 2 mm, pearl shaped). The reaction mixture was subsequently concentrated in a vacuum and purified by column chromatography on silica gel (hexane/diethyl ether 6:1). In addition to 2.25 g of educt, there were obtained 11.9 g (66%) of (RS)-2-(2-buten-1-yl)-5-chloro-6-methoxy-3,3-dimethyl-1-indanone as a pale yellow solid with m.p. 86°.

Provenance & Evidence