[NH2-].[Na+].[C:3]1(=[O:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.N.[C:14]1([CH3:29])[CH:19]=[CH:18][C:17]([C:20](OC2C=CC=CC=2)=[O:21])=[CH:16][CH:15]=1.Cl>CCOCC>[C:14]1([CH3:29])[CH:19]=[CH:18][C:17]([C:20]([CH:4]2[CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]2=[O:12])=[O:21])=[CH:16][CH:15]=1To a suspension of 7.8 g. of sodium amide in 100 ml. anhydrous ether under an atmosphere of nitrogen is added 13.2 g. of indan-1-one. Ammonia is evolved and the mixture is stirred and heated under reflux until evolution ceases, after about 1 hour. A solution of 21.2 g. of phenyl p-toluate in 250 ml. of ether is then added dropwise over a period of 15 min. and the resulting mixture is heated under reflux for 11/2 hr. It is then cooled and poured onto 500 g. of ice, and then made slightly acidic by the addition of 2N hydrochloric acid. The organic layer is separated and washed twice with a 10% solution of sodium bicarbonate and once with water. It is then shaken with a saturated aqueous solution of cupric acetate, and the 2-phase system is stirred vigorously overnight. The resulting brown solid produced is filtered off and added to a stirred mixture of 250 ml. of ether and 100 ml of 2N hydrochloric acid. After 1 hr. the ether layer is separated, washed with sodium bicarbonate solution and water and dried over sodium sulfate. Removal of the ether gives a crude crystalline residue which can be recrystallized from ether to give the title product (m.p. 103°-105°).
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