Ethanol → HCID 23076558, compound

HRID 2221524Notes

Reaction equation

HRID 2221524 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[N:13]=[C:14]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[O:15][C:16]=1[CH3:17])[CH:5]=[O:6].C(O)C.[BH4-].[Na+].O>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[N:13]=[C:14]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[O:15][C:16]=1[CH3:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 23076599HCID 23076599, compound

Product 1

HCID 23076558HCID 23076558, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzaldehyde (4.93 g) in tetrahydrofuran (100 mL)-ethanol (50 mL) was gradually added sodium borohydride (0.51 g) at 0° C. After stirring at room temperature for 2 hrs, water was added to the reaction mixture and the precipitated crystals were collected by filtration to give (3-bromo-4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanol as colorless crystals (4.40 g, yield 89%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 141-142° C.

Workup

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

Sources & evidence

ORD record
ord-e476688fc1ee486bb638751ca6a95dd8
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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