Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3(Methoxycarbonylmethylene)glutaric acid dimethylester

HRID 1816846Notes

Reaction equation

HRID 1816846 reaction equation
[C:1]([CH:5]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH3:4])=[O:2].O=[C:26]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:27][C:28]([O:30][CH3:31])=[O:29]>C1(C)C=CC=CC=1>[CH3:31][O:30][C:28](=[O:29])[CH2:27][C:26](=[CH:5][C:1]([O:3][CH3:4])=[O:2])[CH2:32][C:33]([O:35][CH3:36])=[O:34]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 74591Dimethyl 3-oxoglutarate

Product 1

HCID 120538503(Methoxycarbonylmethylene)glutaric acid dimethylesterYield 77.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Carbomethoxymethylenetriphenylphosphorane (167 g, 0.5 mol) in toluene (600 ml) was treated with dimethyl 3-oxoglutarate (87 g, 0.5 mol) and the reaction heated to 100° C. on an oil bath at 120° C. under an atmosphere of nitrogen for 36 h. The reaction was then concentrated in vacuo and the oily residue triturated with 40/60 petrol ether/diethylether 1:1, 600 ml. Triphenylphosphine oxide precipitated out and the supernatant liquid was decanted/filtered off. The residue on evaporation in vacuo was Kugelrohr distilled under high vacuum Bpt (oven temperature 180-200° C. at 0.2 torr) to give 3-(methoxycarbonylmethylene)glutaric acid dimethylester (89.08 g, 53%).

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. customthe oily residue triturated with 40/60 petrol ether/diethylether 1:1, 600 ml
  3. customTriphenylphosphine oxide precipitated out
  4. filtrationthe supernatant liquid was decanted/filtered off
  5. customThe residue on evaporation in vacuo
  6. distillationdistilled under high vacuum Bpt (oven temperature 180-200° C. at 0.2 torr)

Sources & evidence

ORD record
ord-7873cf50f4d44791b9952ab5f7a932aa
Source dataset
uspto-grants-2009_10
Patent number
US07597875B2

Reaction notes

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