Citric Acid → HCID 22554791, compound

HRID 2087008Notes

Reaction equation

HRID 2087008 reaction equation
[C:1]1([C:9]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([O:16][CH3:17])=[CH:14][CH:13]=2)=[O:10])[CH:8]=[CH:7][C:4]([O:5][CH3:6])=[CH:3][CH:2]=1.[C:20](Cl)(=[O:29])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:6][O:5][C:4]1[CH:3]=[CH:2][C:1]([C:9](=[O:10])[CH:11]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[CH:18][CH:19]=2)[C:20]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[O:29])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 7477p-Anisoyl chlorideHCID 67120Desoxyanisoin

Product 1

HCID 22554791HCID 22554791, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of desoxyanisoin (1.0 equiv.) in THF at −78° C. was added dropwise 1.5 equiv. of [(CH3)2Si]2NLi. The solution was stirred for 1 h at −78° C., followed by addition of 1.2 equiv. of p-anisoyl chloride. The reaction mixture was stirred for 10 min at −78° C. and then for 22 h at rt, acidified with 10% citric acid, and extracted with EtOAc. The combined organic layers were washed with water and dried over Na2SO4. Removal of solvent in vacuo provided a crude solid which was purified by flash chromatography (CH2Cl2) to give 1,2,3-tris(4-methoxyphenyl)propane-1,3-dione.

Workup

  1. stirringThe reaction mixture was stirred for 10 min at −78° C.
  2. waitfor 22 h at rt
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. customRemoval of solvent in vacuo
  7. customprovided a crude solid which
  8. customwas purified by flash chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-6100a5155ec046459543c4ad37c05c27
Source dataset
uspto-grants-2004_04
Patent number
US06727273B2

Reaction notes

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