Water → HCID 86605754, compound

HRID 2221693Notes

Reaction equation

HRID 2221693 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([CH3:28])=[C:15]([CH2:17][O:18][C:19]3[CH:23]=[C:22]([C:24](OC)=[O:25])[O:21][N:20]=3)[N:16]=2)=[CH:8][CH:7]=1)[CH3:2].[BH4-].[Na+].O>CO>[OH:25][CH2:24][C:22]1[O:21][N:20]=[C:19]([O:18][CH2:17][C:15]2[N:16]=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:29])=[CH:7][CH:8]=3)[O:13][C:14]=2[CH3:28])[CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23076427HCID 23076427, compound

Product 1

HCID 86605754HCID 86605754, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-({2-[4-(2-ethoxy-2-oxoethyl)phenyl]-5-methyl-1,3-oxazol-4-yl}methoxy)isoxazole-5-carboxylate (2.02 g) in methanol (25 mL) was gradually added sodium borohydride (250 mg) at 0° C. After stirring at room temperature for 16 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. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:9-1:1, v/v) to give ethyl (4-[4-({[5-(hydroxymethyl)isoxazol-3-yl]oxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl)acetate as colorless crystals (0.95 g, yield 46%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 116-117° 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
  6. washeluted with ethyl acetate-hexane (1:9-1:1

Sources & evidence

ORD record
ord-5c00c01793214bb98b8bed1e705e57ea
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…