Hexane → [1-(6-Benzyloxy-2-naphthylmethyl)-4-phenyl-3-pyrrolyl]methanol

HRID 349894

Reaction equation

HRID 349894 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([CH2:25][N:26]1[CH:30]=[C:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:28]([C:37](OC)=[O:38])=[CH:27]1)[CH:19]=[CH:18]2)[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:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([CH2:25][N:26]1[CH:30]=[C:29]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:28]([CH2:37][OH:38])=[CH:27]1)[CH:19]=[CH:18]2)[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 23024964Methyl 1-(6-benzyloxy-2-naphthylmethyl)-4-phenylpyrrole-3-carboxylate

Product 1

HCID 23024834[1-(6-Benzyloxy-2-naphthylmethyl)-4-phenyl-3-pyrrolyl]methanolYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (0.258 g) was added to a solution of methyl 1-(6-benzyloxy-2-naphthylmethyl)-4-phenylpyrrole-3-carboxylate (3.04 g) in tetrahydrofuran (30 ml) at 0° C., and the mixture was stirred at room temperature for one hour. Sodium sulfate decahydrate (2.19 g) and hexane (30 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-(6-benzyloxy-2-naphthylmethyl)-4-phenyl-3-pyrrolyl]methanol (2.54 g, yield: 89%). This was recrystallized from ethyl acetate-hexane. Melting point: 116–117° 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-893a5b8d331c4781ae8adea75059963c
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Linked notes

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