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

HRID 2221872Notes

Reaction equation

HRID 2221872 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8](OCC)=[O:9])[C:5]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[O:30][CH:31]=[CH:32][CH:33]=4)[O:26][C:27]=3[CH3:28])=[C:17]([O:34][CH3:35])[CH:16]=2)=[N:4]1)[CH3:2].[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.C(OCC)(=O)C>[CH2:1]([N:3]1[CH:7]=[C:6]([CH2:8][OH:9])[C:5]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[N:24]=[C:25]([C:29]4[O:30][CH:31]=[CH:32][CH:33]=4)[O:26][C:27]=3[CH3:28])=[C:17]([O:34][CH3:35])[CH:16]=2)=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 69216020ethyl 1-ethyl-3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1H-pyrazole-4-carboxylate

Product 1

HCID 69217187{1-ethyl-3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1H-pyrazol-4-yl}methanolYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 1-ethyl-3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1H-pyrazole-4-carboxylate (2.80 g) in tetrahydrofuran (50 mL) was added lithium aluminum hydride (0.22 g) at 0° C. and the mixture was stirred at room temperature for 1 hr. Sodium sulfate decahydrate (1.87 g) was added to the reaction mixture, and the mixture was stirred at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate and the precipitate was filtered off. The filtrate was concentrated to give {1-ethyl-3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1H-pyrazol-4-yl}methanol as colorless crystals (2.32 g, yield 91%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 117-118° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. filtrationthe precipitate was filtered off
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-61b269a9b723494c81b50f38be38410b
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…