Triphenylphosphine → HCID 21702069, compound

Participants

Reaction Steps

2.11 g of 5-bromoindan-1-one are suspended in 10 ml of degassed triethylamine with 67.2 mg of palladium(II) acetate and 78.6 mg of triphenylphosphine with 2.12 ml of ethynyltrimethylsilane and the mixture is stirred under reflux for 1 h. The cooled reaction mixture is concentrated, taken up with 20 ml of satd sodium hydrogencarbonate solution and 40 ml of ethyl acetate and the organic phase is washed first with water, then with satd sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated in vacuo, and the residue is chromatographed on silica gel using n-heptane/ethyl acetate 3/1. 5-Trimethylsilanylethynylindan-1-one is obtained, which is dissolved in 25 ml of methanol and stirred at room temperature for 2 h with potassium carbonate. The reaction mixture is concentrated in vacuo; the residue is stirred with 25 ml of satd sodium hydrogencarbonate solution and 50 ml of ethyl acetate, and the organic phase is then separated off and filtered through a clarifying layer. The filtrate is dried over magnesium sulfate and concentrated in vacuo, and the residue is stirred with n-heptane. The precipitate is filtered off with suction and dried in vacuo. 5-Ethynylindan-1-one of melting point 157° C. is obtained.

Provenance & Evidence