Citric Acid → HCID 66643735, compound

HRID 1695429Notes

Reaction equation

HRID 1695429 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:26])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[N:14][O:15][C:16]=2[CH:17]=[O:18])[CH:9]=1)=[O:4].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:26])[N:7]=[C:8]([O:10][CH2:11][C:12]2[C:13]([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)=[N:14][O:15][C:16]=2[CH2:17][OH:18])[CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 86647276HCID 86647276, compound

Product 1

HCID 66643735HCID 66643735, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-[3-(4-fluoro-phenyl)-5-formyl-isoxazol-4-ylmethoxy]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (720 mg, 2.0 mmol) and sodium borohydride (158 mg, 4.0 mmol) in methanol (36 mL) were stirred for 1 h at room temperature. Addition of 10% aqueous citric acid (100 mL) was followed by extraction with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1) afforded the title compound (510 mg, 70%) as a white solid. MS: m/e=420.3 [M+OAc]−.

Workup

  1. extractionwas followed by extraction with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1)

Sources & evidence

ORD record
ord-fe0558ed2431440c8c5c1099e2888d79
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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