Sodium sulfate decahydrate → HCID 69217738, compound

HRID 2221972Notes

Reaction equation

HRID 2221972 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][C:32]=1[O:33][CH2:34][C:35]1[N:36]=[C:37]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:38][C:39]=1[CH3:40])[CH2:6][O:7][C:8]1[C:12](/[CH:13]=[CH:14]/[C:15](OCC)=[O:16])=[CH:11][N:10]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[N:9]=1.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][C:32]=1[O:33][CH2:34][C:35]1[N:36]=[C:37]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:38][C:39]=1[CH3:40])[CH2:6][O:7][C:8]1[C:12](/[CH:13]=[CH:14]/[CH2:15][OH:16])=[CH:11][N:10]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][CH:25]=2)[N:9]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 86605893ethyl (2E)-3-{3-({3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzyl}oxy)-1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}-2-propenoate

Product 1

HCID 69217738HCID 69217738, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (2E)-3-{3-({3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzyl}oxy)-1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}-2-propenoate (0.507 g) in tetrahydrofuran (50 mL) was added diisobutylaluminum hydride (0.95 M hexane solution, 7.0 mL) at room temperature, and the mixture was stirred at room temperature for 1 hr. Sodium sulfate decahydrate (2.14 g) was added to the reaction mixture, and the mixture was further stirred for 2 hrs. After removing the precipitate by filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give (2E)-3-{3-({3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzyl}oxy)-1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl}-2-propen-1-ol as colorless crystals from a fraction eluted with tetrahydrofuran-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless powder (0.300 g, yield 63%). melting point: 118-119° C.

Workup

  1. stirringthe mixture was further stirred for 2 hrs
  2. customAfter removing the precipitate
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c2e04c656eb648119b1d5a980e989831
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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