Ethanol → HCID 23076542, compound

HRID 2221690Notes

Reaction equation

HRID 2221690 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[O:16][C:17]=1[CH3:18])[CH:6]=[O:7].C(O)C.[BH4-].[Na+].O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][OH:7])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[O:16][C:17]=1[CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 23076519HCID 23076519, compound

Product 1

HCID 23076542HCID 23076542, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methoxy-4-{[5-methyl-2-(3-nitrophenyl)-1,3-oxazol-4-yl]methoxy}benzaldehyde (7.51 g) in tetrahydrofuran (100 mL)-ethanol (15 mL) was gradually added sodium borohydride (397 mg) at 0° C. After stirring at room temperature for 6 hrs, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give (3-methoxy-4-{[5-methyl-2-(3-nitrophenyl)-1,3-oxazol-4-yl]methoxy}phenyl)methanol as colorless crystals (5.92 g, yield 78%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 134-135° C.

Workup

  1. customat 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1ad56352777b4051a6f65d44fbdf72ed
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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