Tetrahydrofuran → (2S)-2-methylhexanoic acid >90%ee

HRID 1510986

Reaktionsgleichung

Reaktionsgleichung von HRID 1510986
FC(F)(F)S(O[C@@H:7]([CH3:11])[C:8]([OH:10])=[O:9])(=O)=O.[CH2:14]([Mg]Cl)[CH2:15][CH2:16]C.O1CCC[CH2:21]1>[Cl-].[Zn+2].[Cl-].C(=O)([O-])[O-].[Na+].[Na+]>[CH3:21][C@@H:7]([CH2:11][CH2:14][CH2:15][CH3:16])[C:8]([OH:10])=[O:9]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 59609136(S)-2-trifluoromethanesulfonyloxypropionic acidHCID 178418265HCID 178418265, Verbindung

Produkt 1

HCID 6999860(2S)-2-methylhexanoic acid >90%eeAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10340Sodium CarbonateLösungsmittelHCID 3007855ZincchlorideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a 10 ml Schlenk tube, 5.0 mg of dry zinc chloride was dissolved in 3.0 ml of absolute tetrahydrofuran and cooled to 0° C. under argon. Thereafter, 222 mg of (S)-2-trifluoromethanesulfonyloxypropionic acid (ee 99%) and 1.05 ml of n-butylmagnesium chloride (2.00 M solution in THF) were added in succession and the reaction was stirred for 3 h at 0° C. Thereafter, the reaction mixture was diluted with petroleum ether, saturated sodium carbonate solution was added and the organic phase was separated off. The aqueous phase was acidified with an aqueous 2 M HCl solution, saturated with NaCl and extracted 3 times with 10 ml of diethyl ether. The combined organic phases were dried over MgSO4 and concentrated in vacuo. Pure (S)-2-methylhexanoic acid (ee 99%) was obtained in 92% yield.

Aufarbeitung

  1. additionwas added
  2. customthe organic phase was separated off
  3. extractionextracted 3 times with 10 ml of diethyl ether
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f2bf80dd4c6a4c848b57da854eae0dbc
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08212065B2

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