Potassium Iodide → Methyl 2-(cinnamoylmethyl)-phenylglyoxalate

HRID 2248983Notes

Reaction equation

HRID 2248983 reaction equation
[C:1]([O-:11])(=O)/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[K+].Br[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21](=[O:26])[C:22]([O:24][CH3:25])=[O:23].[I-].[K+]>CN1CCCC1=O>[C:1]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21](=[O:26])[C:22]([O:24][CH3:25])=[O:23])(=[O:11])[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 14697242Methyl 2-[2-(bromomethyl)phenyl]-2-oxoacetateHCID 236754592-Propenoic acid, 3-phenyl-, potassium salt (1:1)

Product 1

HCID 53710718Methyl 2-(cinnamoylmethyl)-phenylglyoxalate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
23 °C

Procedure

10.4 g (56 millimoles) of potassium transcinnamate and 12.0 g (47 millimoles) of methyl orthobromomethylphenylglyoxalate are dissolved in 250 ml of N-methylpyrrolidone, a pinch of potassium iodide is added and the mixture is stirred for 15 hours at room temperature (23° C.). Thereafter, the mixture is poured onto 500 ml of ice water and extracted with 3×200 ml of methyl tert-butyl ether and the organic phase is washed with water, dried over sodium sulfate and evaporated down in a rotary evaporator. The yield of ketoester is 15.0 g (99%). Thin layer chromatographic analysis shows that it is virtually pure.

Workup

  1. extractionextracted with 3×200 ml of methyl tert-butyl ether
  2. washthe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated down in a rotary evaporator

Sources & evidence

ORD record
ord-590a4d7182cb424cb94c5a0c0b7504ac
Source dataset
uspto-grants-1991_08
Patent number
US05041618

Reaction notes

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