Citric Acid → HCID 86641948, compound

HRID 384142Notes

Reaction equation

HRID 384142 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][N:15]=1)C=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)CC([CH2:23][C:24]([OH:26])=O)(C(O)=O)O>O1CCCC1.ICI.C[Li]>[O:26]1[CH2:24][CH:23]1[C:5]1[CH:4]=[CH:3][C:2]([O:1][C:8]2[CH:9]=[CH:10][CH:13]=[CH:14][N:15]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 311Citric AcidHCID 86641947HCID 86641947, compound

Product 1

HCID 86641948HCID 86641948, compound

Reagents, catalysts & solvents 3

HCID 6346DiiodomethaneSolventHCID 8028TetrahydrofuranSolventHCID 178418348HCID 178418348, compoundSolvent

Procedure

To a solution of 2-phenoxyisonicotinaldehyde (378 mg) in tetrahydrofuran (4 ml), 0.228 ml of diiodomethane and 3.8 ml of methyllithium (1.0M diethyl ether solution) were added under ice-cooling, and the reaction solution was stirred at the same temperature for 1 hour. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50/50)) to afford the title compound as a yellow oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50/50))

Sources & evidence

ORD record
ord-d9fdfddf41c74c47ab758605f008997b
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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