Water → Isohexane ethyl acetate

HRID 131559

Reaktionsgleichung

Reaktionsgleichung von HRID 131559
[CH2:1]([O:3][C:4]([CH:6]=P([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22]C=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])[CH3:2].[CH:26](N=C=S)(C)C.BrC(C)C(=O)C(OC)=O.O>C1COCC1>[CH3:20][CH2:25][CH2:24][CH:23]([CH3:22])[CH3:26].[C:4]([O:3][CH2:1][CH3:2])(=[O:5])[CH3:6]

Komponenten

6

Edukt 4

HCID 962WaterHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 75263Isopropyl IsothiocyanateHCID 11183175Methyl 3-bromo-2-oxobutanoate2×

Produkt 1

HCID 21882781Isohexane ethyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Ethoxycarbonylmethylene triphenyl phosphorane (33.8 g) in dry THF (200 ml) was treated with isopropyl isothiocyanate (10.1 g) at 65° C. for 16 h under nitrogen. The mixture was cooled to −78° C. and methyl 3-bromo-2-oxo-butanoate was added. The reaction was allowed to warm slowly to room temperature. After 24 h at room temperature more methyl 3-bromo-2-oxo-butanoate (2.8 g) was added and the mixture was warmed to 60° C. for 16 h. The cooled reaction was poured into water (1.5 L) and extracted into ether. Drying and evaporation gave an oil which was chromatographed (SiO2/10:1 isohexane-ethyl acetate then 5:1 isohexane-ethyl acetate) to afford the subtitle compound (23.5 g). δ 1HCDCl3 1.23-1.35 (9H, m), 2.26 (3H,s), 3.46 (1H, m), 3.82 (3H, s), 4.2 (2H, q), 7.42 (1H, br.s)

Aufarbeitung

  1. temperatureto warm slowly to room temperature
  2. temperaturethe mixture was warmed to 60° C. for 16 h
  3. customThe cooled reaction
  4. extractionextracted into ether
  5. customDrying
  6. customevaporation
  7. customgave an oil which
  8. customwas chromatographed (SiO2/10:1 isohexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-44497de50c15496f9245087358b694ec
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384950B2

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