Methanol → Methyl 2-methyl-3-(methylthio)propionate

HRID 2059064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2059064
[CH3:1][CH:2]([CH2:7][SH:8])[C:3]([O:5][CH3:6])=[O:4].CO.F[C:12](F)(F)COP(OCC(F)(F)F)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>ClCCl>[CH3:6][O:5][C:3](=[O:4])[CH:2]([CH3:1])[CH2:7][S:8][CH3:12]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 49964Triphenylbis(2,2,2-trifluoroethoxy)phosphoraneHCID 107231Methyl 2-methyl-3-mercaptopropionate

Produkt 1

HCID 3018979Methyl 2-methyl-3-(methylthio)propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-methyl-3-mercaptoproponate (1.34 g, 10 mmol) and methanol (0.42 g, 10 mmole) is added to a mixture of bis(2,2,2-trifluoroethoxy)triphenylphosphorane (11 mmole) [prepared in situ from triphenylphosphine (12 mmole) and sodium 2,2,2-trifluoro ethoxide (24 mmole) in dry diethyl ether (20 ml)] in dichloromethane (20 ml). After 20 hours stirring at room temperature the mixture is poured into water and extracted with ether. The ether extract is washed with 5% aqueous sodium hydroxide and dried over magnesium sulfate. The solution is evaporated, solids removed by filtration and the oily residue purified by vacuum distillation yielding methyl-3-methylthio-2-methylpropanoate.

Aufarbeitung

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washis washed with 5% aqueous sodium hydroxide
  4. dry with materialdried over magnesium sulfate
  5. customThe solution is evaporated
  6. customsolids removed by filtration
  7. distillationthe oily residue purified by vacuum distillation

Quellen und Nachweise

ORD-Eintrag
ord-4c9aefd2c98d45e39ec0d413fec1da52
Quelldatensatz
uspto-grants-1982_03
Patentnummer
US04321383

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