Citric Acid → HCID 23159841, compound

HRID 2110835Notes

Reaction equation

HRID 2110835 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=[O:12])[C:4]([CH3:16])=[N:3]1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>COCCOC.O1CCCC1>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]2[CH:9]=[C:10]([CH2:11][OH:12])[CH:13]=[CH:14][CH:15]=2)[C:4]([CH3:16])=[N:3]1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 4311764Sodium borohydrideHCID 23159828HCID 23159828, compound

Product 1

HCID 23159841HCID 23159841, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-(1,3,5-Trimethyl-1H-pyrazol-4-yl)benzaldehyde (2.05 g, 9.57 mmol) was dissolved in a mixed solution of 1,2-dimethoxyethane (10 mL) and tetrahydrofuran (10 mL), sodium borohydride (0.265 g, 7.00 mmol) was added under ice-cooling, and the mixture was stirred under a nitrogen atmosphere at the same temperature for 3 hr. Dilute aqueous citric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (50% ethyl acetate/hexane-ethyl acetate) to give the title compound (1.20 g, yield 58%) as a colorless oil. MS: m/z 217 (MH+).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (50% ethyl acetate/hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1dbc043a375a42c592c1cb04be145e60
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

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