Ethanol → HCID 23076465, compound

HRID 2221546Notes

Reaction equation

HRID 2221546 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[O:22][CH:23]=[CH:24][CH:25]=3)[O:18][C:19]=2[CH3:20])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:2].C(O)C.[BH4-].[Na+].O>O1CCCC1>[O:22]1[CH:23]=[CH:24][CH:25]=[C:21]1[C:17]1[O:18][C:19]([CH3:20])=[C:15]([CH2:14][O:13][C:6]2[CH:5]=[CH:4][C:3]([CH2:1][OH:2])=[CH:12][C:7]=2[C:8]([O:10][CH3:11])=[O:9])[N:16]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 23076605HCID 23076605, compound

Product 1

HCID 23076465HCID 23076465, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-formyl-2-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}benzoate (8.18 g) in tetrahydrofuran (50 mL)-ethanol (50 mL) was gradually added sodium borohydride (0.91 g) at room temperature. After stirring for 2 hrs, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 2-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-5-hydroxymethylbenzoate as pale-yellow crystals (6.53 g, yield 79%) from a fraction eluted with ethyl acetate-hexane (2:1, v/v). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 131-132° C.

Workup

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

Sources & evidence

ORD record
ord-6c819aad7ced425087fd658ee47780fc
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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