Isopropyl iodide → 2-Methyl-3-phenyloctan-4-one
Reaction equation
[C:1]1([CH2:7][C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].I[CH:18]([CH3:20])[CH3:19]>>[CH3:19][CH:18]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8](=[O:13])[CH2:9][CH2:10][CH2:11][CH3:12])[CH3:20]Participants
Procedure
To an ice-cold magnetically stirred mixture of 1-phenylhexan-2-one (Intermediate II-1) (7.04 gram, 0.04 mol) and sodium methoxide (4.32 g, 0.08 mol) was added dropwise 2-iodopropane (15 ml) in a nitrogen atmosphere. The resulting mixture was heated for 1 hour at reflux temperature. The obtained mixture was allowed to attain room temperature and concentrated. The resulting residue was taken up in diethyl ether and water. The diethyl ether layer was separated and successively washed with an aqueous Na2S2O3 solution and water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was further purified using Sepacore equipment: (petroleum ether/diethyl ether=19/1 (v/v)) to give 2-methyl-3-phenyl-octan-4-one (Intermediate IIa-1) (3.52 gram) as a colorless oil; 1H-NMR (400 MHz, CDCl3) δ 0.66 (d, J=7, 3H), 0.81 (t, J=7, 3H), 0.96 (d, J=7, 3H), 1.10-1.24 (m, 2H), 1.36-1.54 (m, 2H), 2.29-2.47 (m, 3H), 3.30 (d, J=10 Hz, 1H), 7.20-7.33 (m, 5H). Rf (petroleum ether/diethyl ether=98/2 (v/v))˜0.25.
Workup
- temperatureThe resulting mixture was heated for 1 hour
- temperatureat reflux temperature
- customto attain room temperature
- concentrationconcentrated
- customThe diethyl ether layer was separated
- washsuccessively washed with an aqueous Na2S2O3 solution and water
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was further purified
Sources & evidence
- ORD record
- ord-c83335719a9a4f3b8367bb1aed3f334d
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410135B2
Reaction notes
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