Hexane → [1-(3,5-Dibenzyloxybenzyl)-4-phenyl-3-pyrrolyl]methanol

HRID 349900Notes

Reaction equation

HRID 349900 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:34]=[C:35]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:36]=1)[CH2:18][N:19]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([C:30](OC)=[O:31])=[CH:20]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>[CH2:38]([O:37][C:35]1[CH:34]=[C:17]([CH:16]=[C:15]([O:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:36]=1)[CH2:18][N:19]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]([CH2:30][OH:31])=[CH:20]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 23025021Methyl 1-(3,5-dibenzyloxybenzyl)-4-phenyl-3-pyrrolecarboxylate

Product 1

HCID 23024986[1-(3,5-Dibenzyloxybenzyl)-4-phenyl-3-pyrrolyl]methanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1.97 g) was added to a solution of methyl 1-(3,5-dibenzyloxybenzyl)-4-phenyl-3-pyrrolecarboxylate (26.2 g) in tetrahydrofuran (250 ml) at 0° C., and the mixture was stirred at room temperature for one hour. Sodium sulfate decahydrate (16.1 g) and hexane (250 ml) were added to the reaction mixture, and the mixture was stirred at room temperature for 30 minutes. After the precipitate was removed by filtration, the filtrate was concentrated. The colorless crystals obtained were collected by filtration to yield [1-(3,5-dibenzyloxybenzyl)-4-phenyl-3-pyrrolyl]methanol (24.20 g, yield: 98%). This was recrystallized from tetrahydrofuran-hexane. Melting point: 115–116° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. customAfter the precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customThe colorless crystals obtained
  5. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-f26aad1cbf9c40d18e487b09846da559
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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