Water → 2-Methyl-3-phenyloct-2-en-4-one
Reaction equation
[CH3:1][CH:2]([C:4](Br)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9])[CH3:3].[Cl-].[Li+].O>CN(C=O)C>[CH3:1][C:2](=[C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
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).
Workup
- customto attain room temperature
- extractionextracted with diethyl ether
- customThe organic layer was separated
- washwashed with water (4 portions)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe obtained residue was purified
Sources & evidence
- ORD record
- ord-7912a6824b984391a5a9019e92f57cfd
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410135B2
Reaction notes
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