Water → 2-Methyl-3-phenyloct-2-en-4-one

Participants

Reaction Conditions

Reaction Steps

The crude 2-methyl-3-bromo-3-phenyloctan-4-one (intermediate IIb-1) was dissolved in magnetically stirred anhydrous DMF (35 ml) under a nitrogen atmosphere. Lithium chloride (3.2 gram, 0.075 mol) was added and the resulting mixture was heated at 130° C. for 90 minutes. The resulting mixture was allowed to attain room temperature and was subsequently poured into water and extracted with diethyl ether. The organic layer was separated and washed with water (4 portions). The organic layer was dried over Na2SO4, filtered and concentrated. The obtained residue was purified using Sepacore equipment: (petroleum ether/diethyl ether=98/2 (v/v)) to give 2-methyl-3-phenyloct-2-en-4-one (Intermediate III-1) (1.96 gram, 46% yield) as a pale yellow oil; 1H-NMR (400 MHz, CDCl3) δ 0.81 (d, J=7, 3H), 1.13-1.24 (m, 2H), 1.43-1.52 (m, 2H), 1.66 (s, 3H), 2.00 (s, 3H), 2.25 (t, J=7, 2H), 7.15 (br d, J=8, 2H), 7.20-7.39 (m, 3H).

Provenance & Evidence