Hexane → HCID 69423063, compound

HRID 349985Notes

Reaction equation

HRID 349985 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:38]=[CH:37][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([C:25](OCC)=[O:26])[C:22]([C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[N:21]2)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].CCCCCC>O1CCCC1>[CH2:7]([O:14][C:15]1[CH:38]=[CH:37][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([CH2:25][OH:26])[C:22]([C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)=[N:21]2)=[CH:17][CH:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23024738HCID 23024738, compound

Product 1

HCID 69423063HCID 69423063, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1.33 g) was added to a solution of ethyl 1-(4-benzyloxybenzyl)-3-(4-fluorophenyl)-1H-pyrazole-4-carboxylate (15.1 g) in tetrahydrofuran (300 ml) at 0° C., which was stirred at room temperature for 1 hour. Sodium sulfate decahydrate (12.26 g) and hexane (100 ml) was added to the reaction mixture, which was stirred at room temperature for 1 hour. After the precipitate was removed by filtration, the filtrate was concentrated to obtain 1-(4-benzyloxybenzyl)-3-(4-fluorophenyl)-1H-pyrazol-4-ylmethanol (12.9 g, yield 95%) as colorless crystals. This was recrystallized from ethyl acetate-hexane. Melting point: 112–113° C.

Workup

  1. stirringwas stirred at room temperature for 1 hour
  2. customAfter the precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ddb74aa6cc80416d83a23c476903228a
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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