Sodium sulfate decahydrate → (3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazol-4-yl)methanol

HRID 2221950Notes

Reaction equation

HRID 2221950 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[N:25]=[C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:27][C:28]=1[CH3:29])[CH2:6][O:7][C:8]1[C:12]([C:13](OCC)=[O:14])=[CH:11][N:10]([CH3:18])[N:9]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].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:19]=[CH:20][C:21]=1[O:22][CH2:23][C:24]1[N:25]=[C:26]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[O:27][C:28]=1[CH3:29])[CH2:6][O:7][C:8]1[C:12]([CH2:13][OH:14])=[CH:11][N:10]([CH3:18])[N:9]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23076506HCID 23076506, compound

Product 1

HCID 69214986(3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazol-4-yl)methanolYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazole-4-carboxylate (4.40 g) in tetrahydrofuran (20 mL) was gradually added lithium aluminum hydride (350 mg) at 0° C., and the mixture was stirred for 30 min. Sodium sulfate decahydrate (3.54 g) was added to the reaction mixture, the precipitate was filtered off, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give (3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazol-4-yl)methanol (3.88 g, yield 97%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 108-109° C.

Workup

  1. customat 0° C.
  2. filtrationthe precipitate was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-757cb81af2944cffb1734e1367f93c4f
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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