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

HRID 350022Notes

Reaction equation

HRID 350022 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2[S:14][CH:15]=[C:16]([CH2:18][O:19][C:20]3[CH:41]=[CH:40][C:23]([CH2:24][N:25]4[CH:29]=[C:28]([C:30](OCC)=[O:31])[C:27]([C:35]5[S:36][CH:37]=[CH:38][CH:39]=5)=[N:26]4)=[CH:22][CH:21]=3)[N:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:7]1([C:13]2[S:14][CH:15]=[C:16]([CH2:18][O:19][C:20]3[CH:41]=[CH:40][C:23]([CH2:24][N:25]4[CH:29]=[C:28]([CH2:30][OH:31])[C:27]([C:35]5[S:36][CH:37]=[CH:38][CH:39]=5)=[N:26]4)=[CH:22][CH:21]=3)[N:17]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23024852ethyl 1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 69420295[1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]methanolYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (540 mg) was added gradually to a solution of ethyl 1-[4-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazole-4-carboxylate (7.10 g) in tetrahydrofuran (50 ml) at 0° C., which was stirred for 30 minutes. Sodium sulfate decahydrate (4.33 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-(2-phenyl-4-thiazolylmethoxy)benzyl]-3-(2-thienyl)-1H-pyrazol-4-yl]methanol (6.31 g, yield: 96%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 147˜148° C.

Workup

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

Sources & evidence

ORD record
ord-356a7fe4ba894eefb156db07f4cc6b7b
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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