Sodium sulfate decahydrate → [1-[6-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethyl]-4-phenyl-3-pyrrolyl]methanol

HRID 349994

Reaction equation

HRID 349994 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][N:28]2[CH:32]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:30]([C:39](OC)=[O:40])=[CH:29]2)=[CH:23][CH:22]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[N:10][C:9]=1[CH2:19][O:20][C:21]1[N:26]=[CH:25][C:24]([CH2:27][N:28]2[CH:32]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:30]([CH2:39][OH:40])=[CH:29]2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 69423340Methyl 1-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethyl]-4-phenylpyrrole-3-carboxylate

Product 1

HCID 69422752[1-[6-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethyl]-4-phenyl-3-pyrrolyl]methanolYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (205 mg) was added gradually to a solution of methyl 1-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethyl]-4-phenylpyrrole-3-carboxylate (1.30 g) in tetrahydrofuran (40 ml) at 0° C., and the resultant was stirred for 3 hours. Sodium sulfate decahydrate (2.80 g) was added to the reaction mixture, and the precipitate was removed by filtration. The filtrate was concentrated, and the residue was subjected to silica gel column chromatography to obtain [1-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-3-pyridylmethyl]-4-phenyl-3-pyrrolyl]methanol (1.15 g, yield 94%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (3:2, volume ratio).

Workup

  1. customthe precipitate was removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-464073a1055e4e83b01ab7735a14d550
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Linked notes

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