4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde → 1-[4-Methyl-2-(4-trifluoromethylphenyl)thiazol-5-yl]ethanol
Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[S:5][C:6]=1[CH:7]=[O:8].[CH3:19][Mg]Br>O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=2)[S:5][C:6]=1[CH:7]([OH:8])[CH3:19]Participants
4
Procedure
2.5 g 4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbaldehyde were dissolved in 100 ml tetrahydrofuran. At 0° C. 3.38 ml of an one molar solution of methylmagnesium bromide in tetrahydrofuran were added dropwise. The cooling bath was removed and the reaction mixture stirred at room temperature for one hour. Then the reaction mixture was poured on 100 ml ice cold saturated NH4Cl solution and extracted five times with portions of 80 ml ethyl acetate. The combined organic layers were washed with 100 ml brine then dried over MgSO4. The solvent was evaporated to obtain 2.7 g crude 1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol as pale yellow solid which was used without further purification.
Workup
- customAt 0° C
- customThe cooling bath was removed
- additionThen the reaction mixture was poured on 100 ml ice cold saturated NH4Cl solution
- extractionextracted five times with portions of 80 ml ethyl acetate
- washThe combined organic layers were washed with 100 ml brine
- dry with materialthen dried over MgSO4
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-9eb2c0d290ce4c1cb41290274ec0a5ac
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834030B2
Reaction notes
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