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

HRID 1744413

Reaktionsgleichung

Reaktionsgleichung von HRID 1744413
[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]

Komponenten

6

Edukt 2

HCID 111372772-Propenoic acid, 2-(acetyloxy)-, methyl esterHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 11051803(S)-methyl 2-methylcarbonyloxypropanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 139283DiphosphaneLösungsmittelHCID 10915722Bis(norbornadiene)rhodium(I) tetrafluoroborateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0489fe46fcc448b680af3d1bea2f9f8d
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015342B2

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