Tetrahydrofuran → Ethyl 2-[4-(trifluoromethoxy)phenyl]-5-thiazolecarboxylate
Reaction equation
[Al].[Li].[F:3][C:4]([F:25])([F:24])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:13][CH:14]=[C:15](C(OCC(C)C)=O)[N:16]=2)=[CH:8][CH:7]=1.[OH2:26].O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[O:43]1[CH2:47][CH2:46]C[CH2:44]1>>[F:25][C:4]([F:3])([F:24])[O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:13][C:14]([C:44]([O:43][CH2:47][CH3:46])=[O:26])=[CH:15][N:16]=2)=[CH:10][CH:11]=1Participants
5
Procedure
Lithium aluminum hidride (2.0 M solution in tetrahydrofuran) (2.81 mL) was added to a solution of 2-methylpropyl 2-[4-(trifluoromethoxy)phenyl]-1,3-thiazole-4-carboxylate (881 mg) in tetrahydrofuran (15 mL), and the mixture was stirred at room temperature for 30 min. Sodium sulfate decahydrate was added portionwise and an additional amount of tetrahydrofuran was added, and the mixture was stirred for 1.5 hr. The reaction mixture was filtered through Celite and the solvent was then distilled off under reduced pressure. The resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=98:2-25:75) to afford the title compound (361 mg).
Workup
- stirringthe mixture was stirred for 1.5 hr
- filtrationThe reaction mixture was filtered through Celite
- distillationthe solvent was then distilled off under reduced pressure
- customThe resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=98:2-25:75)
Sources & evidence
- ORD record
- ord-0f7bc148125247aab3168f8b2eb374f9
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729271B2
Reaction notes
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