[2-(4-Trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazol-5-yl]-methanol → 2-(4-Trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazole-5-carbaldehyde
Reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([CH2:25][OH:26])=[C:12]([CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([C:21]([F:24])([F:23])[F:22])[CH2:17][CH2:16]3)[N:13]=2)=[CH:5][CH:4]=1>ClCCl.[O-2].[Mn+4].[O-2]>[F:28][C:2]([F:1])([F:27])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]([CH:25]=[O:26])=[C:12]([CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([C:21]([F:23])([F:22])[F:24])[CH2:17][CH2:16]3)[N:13]=2)=[CH:5][CH:4]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 1 g of [[2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazol-5-yl]-methanol in 7 ml of dichloromethane was added 2.35 g of manganese(IV)oxide (activated with charcoal). The resulting mixture was heated under reflux for four hours. The cooled reaction mixture was filtered through a pad of celite. The filtrate was concentrated under reduced pressure and purified by column chromatography on silica gel (heptane 80/ethyl acetate 20) to give 0.53 g of 2-(4-trifluoromethyl-phenyl)-4-(4-trifluoromethyl-piperidin-1-ylmethyl)-thiazole-5-carbaldehyde.
Workup
- temperatureThe resulting mixture was heated
- temperatureunder reflux for four hours
- customThe cooled reaction mixture
- filtrationwas filtered through a pad of celite
- concentrationThe filtrate was concentrated under reduced pressure
- custompurified by column chromatography on silica gel (heptane 80/ethyl acetate 20)
Sources & evidence
- ORD record
- ord-bbdd75a739da4c9b88e1e5cd94c3beb9
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834030B2
Reaction notes
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