(2-(Benzyloxy)-3-tert-butylphenyl)(3-(pyridin-2-yl)phenyl)methanol → (2-(Benzyloxy)-3-tert-butylphenyl)(3-(pyridin-2-yl)phenyl)methanone
Reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH:22]=1)[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH:22]=1)=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Procedure
A solution of crude 3 (10.25 mmol) in dichloromethane (160 mL) was treated with manganese dioxide (14 g, 15 equiv.) and this suspension was stirred under reflux for 6 hr. The reaction mixture was filtered through Celite and the filter cake was washed with ethyl acetate. The solvent was removed on a rotary evaporator and the crude product was purified by chromatography on silica (110 g) with 5% ethyl acetate in heptane (5 L) to produce 4 (2.75 g, 64% over 2 steps).
Workup
- temperatureunder reflux for 6 hr
- filtrationThe reaction mixture was filtered through Celite
- washthe filter cake was washed with ethyl acetate
- customThe solvent was removed on a rotary evaporator
- customthe crude product was purified by chromatography on silica (110 g) with 5% ethyl acetate in heptane (5 L)
- customto produce 4 (2.75 g, 64% over 2 steps)
Sources & evidence
- ORD record
- ord-6d9c85febd71411d978afb7779d446c3
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541522B2
Reaction notes
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