Dimethylformamide → 5-Hydroxy-6-methoxy-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

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Reaction Conditions

Reaction Steps

In a three necked reaction flask equipped with a reflux condenser, a mixture of 5 g of 2,3-dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-one (see example 1) and 5.5 g of sodium cyanide in 44.5 ml of dimethyl formamide was stirred at 100° C. for 40 hours. Then, the mixture was pored on an aqueous NaH2PO4 solution and extracted 4 times with ethyl acetate, dried over Na2CO3, and concentrated. The raw product was chromatographed in methylene chloride containing 1% of methanol to yield 2.5 g of white crystals. m.p. 105-107° C. MS: 206(M+), 191(100%), 163, 131, 103.

Provenance & Evidence