2-Propenoic acid, 2-(acetyloxy)-, methyl ester → (S)-methyl 2-methylcarbonyloxypropanoate

HRID 1744413Notes

Reaction equation

HRID 1744413 reaction equation
[C:1]([O:4][C:5](=[CH2:10])[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].[H][H]>[B-](F)(F)(F)F.C1C2C=CC1C=C2.C1C2C=CC1C=C2.[Rh].PP.CO>[CH3:2][C:1]([O:4][C@@H:5]([CH3:10])[C:6]([O:8][CH3:9])=[O:7])=[O:3]

Participants

6

Reactant 2

HCID 111372772-Propenoic acid, 2-(acetyloxy)-, methyl esterHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11051803(S)-methyl 2-methylcarbonyloxypropanoate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 139283DiphosphaneSolventHCID 10915722Bis(norbornadiene)rhodium(I) tetrafluoroborateSolvent

Procedure

In a 50 ml Schlenk vessel, Rh(nbd)2BF4 (5.2 mg, 1 mol %) and the diphosphine ligand (1 mol %) were dissolved in MeOH (10 ml) under argon. After all of the rhodium complex had gone into solution, methyl 2-acetoxyacrylate (200 mg, 1.39 mmol) was added. The Schienk 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 20 h and the solvent was then distilled off in an oil pump vacuum. The residue was purified by bulb tube distillation. The ester (S)-8 was obtained as a colorless oil in quantitative yield.

Workup

  1. additionwas added
  2. distillationthe solvent was then distilled off in an oil pump vacuum
  3. customThe residue was purified by bulb tube
  4. distillationdistillation

Sources & evidence

ORD record
ord-0489fe46fcc448b680af3d1bea2f9f8d
Source dataset
uspto-grants-2006_03
Patent number
US07015342B2

Reaction notes

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