Hexane → [1-(4-Benzyloxybenzyl)-4-phenyl-3-pyrrolyl]methanol

HRID 349887Notes

Reaction equation

HRID 349887 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:36]=[CH:35][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:22]([C:31](OC)=[O:32])=[CH: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:36]=[CH:35][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:22]([CH2:31][OH:32])=[CH: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 23024961Methyl 1-(4-benzyloxybenzyl)-4-phenylpyrrole-3-carboxylate

Product 1

HCID 23025097[1-(4-Benzyloxybenzyl)-4-phenyl-3-pyrrolyl]methanolYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (2.53 g) was added to a solution of methyl 1-(4-benzyloxybenzyl)-4-phenylpyrrole-3-carboxylate (21.52 g) in tetrahydrofuran (100 ml) at 0° C., and the mixture was stirred at room temperature for one hour. Sodium sulfate decahydrate (30.00 g) and hexane (100 ml) were added to the reaction mixture and the mixture was stirred at room temperature for one hour. After the precipitate was removed by filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and [1-(4-benzyloxybenzyl)-4-phenyl-3-pyrrolyl]methanol (19.68 g, yield: 98%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 122–123° C.

Workup

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

Sources & evidence

ORD record
ord-09d6ae465fc24d6e9337f9e4b92d37a2
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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