CC(C)([O-])C.[K+].CCOCC.[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][CH2:20][C:21]2=[O:24])=[CH:16][CH:15]=1.[N:25](OCCC(C)C)=[O:26]>C(O)C.C(O)(C)(C)C>[CH3:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][C:20](=[N:25][OH:26])[C:21]2=[O:24])=[CH:16][CH:15]=1
A mixture of potassium tert-butoxide (11.5 gm, 0.1 m), ether (400 ml), tert-butanol (15 ml) and absolute ethanol (15 ml) was refluxed for 1/2 hour to insure complete solution of the potassium tert-butoxide. To the hot solution was added 7-methoxy-1-tetralone (17.6 gms, 0.1 m) and the reaction mixture turned from yellow to dark brown. To this refluxing solution was added isopentyl nitrite (19 ml). During this addition external heating was not necessary because of the exothermic nature of the reaction. The reaction mixture was refluxed for 1/2 hour during which time the walls of the flask became coated with a brown solid. After cooling in an ice-bath, the solvent was removed by decantation. To the solid was added aqueous hydrogen chloride (1 N, 200 ml). After stirring 1/2 hour, the brown solid was filtered to yield 10 gms (50%) of product.
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