Water → 2-(4-Hydroxy-3-methylphenyl)-2-methyl-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}propan-1-one
Reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:29])([CH3:28])[C:10]([C:12]2[S:13][C:14]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)=[CH:15][C:16]=2[CH3:17])=[O:11])=[CH:5][C:4]=1[CH3:30].Cl.N1C=CC=CC=1.O>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:28])([CH3:29])[C:10]([C:12]2[S:13][C:14]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:20][CH:19]=3)=[CH:15][C:16]=2[CH3:17])=[O:11])=[CH:5][C:4]=1[CH3:30]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To 2-(4-methoxy-3-methylphenyl)-2-methyl-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}propan-1-one (intermediate 104, 0.35 g) in a pressure vessel was added pyridine hydrochloride (10 g), the vessel was sealed and heated to 150° C. for 72 hours. The reaction vessel was then allowed to cool to room temperature and the solid residue partioned between water and CH2Cl2, the aqueous extract was further extracted CH2Cl2. The combined organic extracts were dried (Na2SO4), filtered and evaporated to yield a brown oil. Purification by flash column chromatography eluting with 1% EtOAc/cyclohexane yielded the title compound as a pale yellow oil.
Workup
- customthe vessel was sealed
- temperatureto cool to room temperature
- extractionthe aqueous extract
- dry with materialThe combined organic extracts were dried (Na2SO4)
- filtrationfiltered
- customevaporated
- customto yield a brown oil
- customPurification by flash column chromatography
- washeluting with 1% EtOAc/cyclohexane
Sources & evidence
- ORD record
- ord-a446494c32bd4380ab4328862f822cd6
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091237B2
Reaction notes
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