Water → HCID 59587569, compound

HRID 1410422Notes

Reaction equation

HRID 1410422 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:35])[C:10](=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1.O.[OH:37]OS([O-])=O.[K+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:35])[C:10](=[O:37])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12521848HCID 12521848, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 59587569HCID 59587569, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(4-methoxyphenyl)-3-oxo-2-(triphenylphosphoranylidene)propionate. (0.510 g, 1.1 mmol) in THF (10 ml) was added water (10 ml) followed by oxone (0.974 g, 1.6 mmol) in portions and the resulting mixture was stirred at room temperature overnight. The solid was removed by filtration and filtrate concentrated in vacuo and extracted with DCM. The combined organic phases were dried over MgSO4 and the solvent removed in vacuo to afford crude ethyl 3-(4-methoxyphenyl)-2,3-dioxopropanoate as a yellow oil (0.500 g) as a mixture with triphenylphosphine oxide which was used without further purification. LCMS (2) 2.38 min; m/z 237.

Workup

  1. customThe solid was removed by filtration and filtrate
  2. concentrationconcentrated in vacuo
  3. extractionextracted with DCM
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6ebff587450a4b6da5cf1112ced7c6c4
Source dataset
uspto-grants-2014_12
Patent number
US08921544B2

Reaction notes

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