Dimethyl Sulfide → HCID 54570347, compound

Participants

Reaction Steps

With stirring, 6 ml of dimethyl sulphide are added at 0° C in an atmosphere of nitrogen to a suspension of 8.05 g of N-chlorosuccinimide in 200 ml of absolute toluene and then at -25° C a solution of 12 g of crude 5-hydroxymethylphenyl-6-methoxy-indane-1-carboxylic acid methyl ester in 50 ml of absolute toluene is added. Upon completion of the addition, the mixture is further stirred for 90 minutes at -25° C. Then 8.3 ml of triethylamine are added to the reaction solution, which is stirred for a further 5 minutes and partitioned between 2 × 100 ml of 2 normal hydrochloric acid and 2 × 100 ml of ether. The organic phases are washed neutral, dried over sodium sulphate and evaporated to dryness in vacuo. The residue is chromatographed on silica gel with methylene chloride as eluant to yield 5-benzoyl-6-methoxy-indane-1-carboxylic acid methyl ester.

Provenance & Evidence