Dimethyl itaconate → Butanedioic acid, 2-methyl-, 1,4-dimethyl ester

HRID 1744412Notes

Reaction equation

HRID 1744412 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])=[CH2:3].[H][H]>[B-](F)(F)(F)F.C1C2C=CC1C=C2.C1C2C=CC1C=C2.[Rh].PP.C1(C)C=CC=CC=1.CO.CO>[CH3:3][CH:2]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:1]([O:10][CH3:11])=[O:9]

Participants

7

Reactant 2

HCID 69240Dimethyl itaconateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 15350Butanedioic acid, 2-methyl-, 1,4-dimethyl ester

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 139283DiphosphaneSolventHCID 10915722Bis(norbornadiene)rhodium(I) tetrafluoroborateSolventHCID 21867641Toluene methanolSolvent

Procedure

In a 50 ml Schlenk vessel, Rh(nbd)2BF4 (4.7 mg, 1 mol %) and the diphosphine ligand (1 mol %) were dissolved in toluene/MeOH (6 ml, 5:1) under argon. After all of the rhodium complex had gone into solution, dimethyl itaconate (200 mg, 1.26 mmol) dissolved in MeOH (4 ml) was added. The Schlenk vessel was subsequently connected via a three-way stopcock with a hydrogen balloon and an oil pump and the inert gas atmosphere was replaced by hydrogen. The reaction mixture was stirred at room temperature for the time indicated and the solvent was then distilled off on a rotary evaporator. The residue was filtered through a short silica gel column (eluent: diethyl ether). Compound (R)-7 was obtained as a colorless oil in quantitative yield.

Workup

  1. additionwas added
  2. distillationthe solvent was then distilled off on a rotary evaporator
  3. filtrationThe residue was filtered through a short silica gel column (eluent: diethyl ether)
  4. customwas obtained as a colorless oil in quantitative yield

Sources & evidence

ORD record
ord-d4b2c0d354ce469fba8daef67460cea9
Source dataset
uspto-grants-2006_03
Patent number
US07015342B2

Reaction notes

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