Diisobutylaluminum hydride → (4-(Trifluoromethyl)-1,3-thiazol-2-yl)methanol
Reaction equation
C([O:3][C:4]([C:6]1[S:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[N:10]=1)=O)C.CC(C[AlH]CC(C)C)C>C1COCC1>[F:14][C:11]([F:12])([F:13])[C:9]1[N:10]=[C:6]([CH2:4][OH:3])[S:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
4-Trifluoromethyl-thiazole-2-carboxylic acid ethyl ester (131 mg) was dissolved in THF (5 ml). The reaction mixture was then cooled to −78° C. DIBAL-H (4.7 ml, 1.0 M in tetrahydrofurane) was added slowly during a period of 10 min. The cooling bath was removed, and the solution was kept under stirring for 30 min at RT. The solution was then cooled to 0° C., and NaF (784 mg) was added, followed by the slow addition of 3 ml water. The product was extracted by ethyl acetate. The solvent was removed, and the crude product was used in alkylation reactions without further purification.
Workup
- customThe cooling bath was removed
- temperatureThe solution was then cooled to 0° C.
- additionNaF (784 mg) was added
- additionfollowed by the slow addition of 3 ml water
- extractionThe product was extracted by ethyl acetate
- customThe solvent was removed
- customthe crude product was used in alkylation reactions without further purification
Sources & evidence
- ORD record
- ord-72c93f292b324972a66dfae5f58af0b6
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283479B2
Reaction notes
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