Ethanol → HCID 23076452, compound

HRID 2221511Notes

Reaction equation

HRID 2221511 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[N:15]=[C:16]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)[O:17][C:18]=1[CH3:19])[CH:7]=[O:8])[CH3:2].C(O)C.[BH4-].[Na+].O>O1CCCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[N:15]=[C:16]([C:20]2[O:21][CH:22]=[CH:23][CH:24]=2)[O:17][C:18]=1[CH3:19])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 85954512HCID 85954512, compound

Product 1

HCID 23076452HCID 23076452, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-ethoxy-4-[[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy]benzaldehyde (20.00 g) in tetrahydrofuran (250 mL)-ethanol (100 mL) was gradually added sodium borohydride (2.31 g) at 0° C. After stirring at room temperature for 1 hr, water was added to the reaction mixture and the precipitated crystals were collected by filtration to give (3-ethoxy-4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanol as pale-yellow crystals (18.80 g, yield 93%). 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-e563de1ce7014b6d84d4a6298a35f8b9
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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