Ethanol → (4-([2-(2-Furyl)-1,3-oxazol-4-yl]methoxy)-3-methoxyphenyl)methanol

HRID 2221507Notes

Reaction equation

HRID 2221507 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][CH:8]=[C:9]([CH2:11][O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=2[O:21][CH3:22])[N:10]=1.C(O)C.[BH4-].[Na+].O>O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][CH:8]=[C:9]([CH2:11][O:12][C:13]2[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][C:14]=2[O:21][CH3:22])[N:10]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 866057054-{[2-(2-Furyl)-1,3-oxazol-4-yl]methoxy}-3-methoxybenzaldehyde

Product 1

HCID 69215267(4-([2-(2-Furyl)-1,3-oxazol-4-yl]methoxy)-3-methoxyphenyl)methanolYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-{[2-(2-furyl)-1,3-oxazol-4-yl]methoxy}-3-methoxybenzaldehyde (9.70 g) in tetrahydrofuran (100 mL)-ethanol (50 mL) was gradually added sodium borohydride (1.23 g) at room temperature. After stirring at room temperature for 30 min., water was added to the reaction mixture and the precipitated crystals were collected by filtration to give (4-{[2-(2-furyl)-1,3-oxazol-4-yl]methoxy}-3-methoxyphenyl)methanol as pale-brown crystals (8.40 g, yield 86%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 117-118° C.

Workup

  1. customat room temperature
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-01be4d968ba447338367c0917c83d519
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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