Ammonium Chloride → HCID 57125638, compound

Reaction equation

CC(C)([O-])C.[K+].[CH3:7][C:8](=[CH:12][CH2:13][CH:14]1[CH2:19][CH:18]2[C:16]([CH3:20])([CH2:17]2)[C:15]1([CH3:22])[CH3:21])[C:9](=[O:11])[CH3:10].[Cl-].[NH4+]>O1CCCC1>[CH3:7][CH:8]([CH:12]=[CH:13][CH:14]1[CH2:19][CH:18]2[C:16]([CH3:20])([CH2:17]2)[C:15]1([CH3:21])[CH3:22])[C:9](=[O:11])[CH3:10]

Participants

Procedure

66.0 g of potassium tert-butoxide dissolved in 850 ml of tetrahydrofuran was added to the solution of 140 g (0.64 mol; 70% pure) of 3-methyl-5-(1,2,2-trimethylbicyclo-[3.1.0]hex-3-yl)pent-3-en-2-one in 850 ml of the same solvent at 0° C. After 30 minutes of stirring at room temperature the reaction mixture was poured on 1 1 of aqueous ammonium chloride solution. After the usual workup the crude product was purified by flash chromatography on silica gel (eluent: hexane/MTBE 19:1) to give three fractions: 5.1, 28.1 and 22.3 g containing respectively 36, 78, and 92% of 3-methyl-5-(1,2,2-trimethylbicyclo[3.1.0]hex-3-yl)pent-4-en-2-one (-40% yield).