Sodium sulfate decahydrate → (3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)methanol

HRID 1295275Notes

Reaction equation

HRID 1295275 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14](OC)=[O:15])[N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Li+].[Al+3].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([CH2:14][OH:15])[N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 22930789methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylate

Product 1

HCID 22930692(3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)methanolYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylate (14.53 g) and tetrahydrofuran (300 ml) was slowly added aluminum lithium hydride (1.79 g) at 0° C. and the mixture was stirred at room temperature for 1 hr. Sodium sulfate 10 hydrate (15.20 g) was slowly added to the reaction mixture at 0° C. and the mixture was stirred at room temperature for 30 min. Insoluble materials were filtered off and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and (3-benzyloxy-1-phenyl-1H-pyrazol-5-yl)methanol (11.65 g, yield 88%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 87–88° C.

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. filtrationInsoluble materials were filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-466c6d29229a4551bb07d349321b420e
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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