Ethanol → HCID 69214329, compound

HRID 2221792Notes

Reaction equation

HRID 2221792 reaction equation
[C:1]1([C:7]2[O:8][C:9]([CH3:35])=[C:10]([CH2:12][O:13][C:14]3[CH:34]=[CH:33][C:17]([CH2:18][O:19][C:20]4[C:24]([CH:25]=[O:26])=[CH:23][N:22]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[N:21]=4)=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[BH4-].[Na+].O>O1CCCC1>[C:1]1([C:7]2[O:8][C:9]([CH3:35])=[C:10]([CH2:12][O:13][C:14]3[CH:15]=[CH:16][C:17]([CH2:18][O:19][C:20]4[C:24]([CH2:25][OH:26])=[CH:23][N:22]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[N:21]=4)=[CH:33][CH:34]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 86605777HCID 86605777, compound

Product 1

HCID 69214329HCID 69214329, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-({4-[(2-phenyl-5-methyl-1,3-oxazol-4-yl)methoxy]benzyl}oxy)-1-phenyl-1H-pyrazole-4-carbaldehyde (0.50 g) in tetrahydrofuran (5 mL)-ethanol (10 mL) was gradually added sodium borohydride (0.040 g) at 0° C. After stirring the reaction mixture at room temperature for 1 hr, water was added, and the precipitated crystals were collected by filtration to give [3-({4-[(2-phenyl-5-methyl-1,3-oxazol-4-yl)methoxy]benzyl}oxy)-1-phenyl-1H-pyrazol-4-yl]methanol as colorless crystals (0.50 g, yield 98%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 118-119° C.

Workup

  1. customat 0° C
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-4a7b5907e1644291ac4501e35c861829
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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