Sodium sulfate decahydrate → [1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]methanol

HRID 350020Notes

Reaction equation

HRID 350020 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[CH:42]=[CH:41][C:24]([CH2:25][N:26]2[CH:30]=[C:29]([C:31](OCC)=[O:32])[C:28]([C:36]3[S:37][CH:38]=[CH:39][CH:40]=3)=[N:27]2)=[CH:23][CH:22]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:25][N:26]2[CH:30]=[C:29]([CH2:31][OH:32])[C:28]([C:36]3[S:37][CH:38]=[CH:39][CH:40]=3)=[N:27]2)=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23024863ethyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 69424441[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]methanolYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1100 mg) was added gradually to a solution of ethyl 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carboxylate (14.39 g) in tetrahydrofuran (50 ml) at 0° C., which was stirred for 30 minutes. Sodium sulfate decahydrate (12.14 g) was added to the reaction mixture, and the precipitate was removed by filtration. The filtrate was concentrated, and the residue was subjected to silica gel column chromatography to obtain [1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]methanol (12.20 g, yield: 93%) as pale yellow oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. customthe precipitate was removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ecdf41d8dd7b4daf8acadf5b85d25002
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

Loading…