Citric Acid → HCID 19081532, compound

HRID 963415Notes

Reaction equation

HRID 963415 reaction equation
[K+].[C:2]([O:8][CH3:9])(=[O:7])[CH2:3][C:4]([O-:6])=O.C[Si](Cl)(C)C.N1(C2CCCCCCCCCC2)CCCCCCCC[CH2:17]N1.[I:37][C:38]1[CH:39]=[C:40]([CH:44]=[C:45]([O:49][CH3:50])[C:46]=1[O:47][CH3:48])C(Cl)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(#N)C>[I:37][C:38]1[CH:39]=[C:40]([C:4](=[O:6])[CH2:3][C:2]([O:8][CH2:9][CH3:17])=[O:7])[CH:44]=[C:45]([O:49][CH3:50])[C:46]=1[O:47][CH3:48]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 6397ChlorotrimethylsilaneHCID 2724687Potassium methyl malonateHCID 19081615HCID 19081615, compoundHCID 57346892Diazabicycloundecane

Product 1

HCID 19081532HCID 19081532, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

272 mg of monomethyl malonate potassium salt and 0.41 ml of trimethylsilyl chloride are stirred at room temperature in 5 ml of acetonitrile for 4 hrs. Subsequently, the mixture is cooled to 0° and 0.75 ml of diaza-bicycloundecane is added. The mixture is stirred at room temperature for 30 min. Thereafter, 0.5 g of 3-iodo-4,5-dimethoxy-benzoyl chloride is added portionwise thereto and the mixture is stirred at room temperature for 19 hrs. The mixture is brought to about pH4 with 10 percent citric acid and extracted three times with ethyl acetate. Chromatography on silica gel with ethyl acetate/hexane 1:1 gives 126 mg of ethyl 3-(3-iodo-4,5-dimethoxy-phenyl)-3-oxo-propionate as a yellowish oil (Keto/Enol mixture). Yield: 26%. Mass spectrum: peaks inter alia at m/e: 378 (M+, 40%); 291 (100%).

Workup

  1. temperatureSubsequently, the mixture is cooled to 0°
  2. stirringthe mixture is stirred at room temperature for 19 hrs
  3. extractionextracted three times with ethyl acetate

Sources & evidence

ORD record
ord-acaffd2889154b99b6e36cb72d8a7ec2
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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