Methanol → Acetic acid 2-ethyl-3-oxo-butyl ester

HRID 12486

Reaktionsgleichung

Reaktionsgleichung von HRID 12486
[OH:1][CH2:2][CH:3]([CH2:7][CH3:8])[C:4](=[O:6])[CH3:5].[C:9](OC(=O)C)(=[O:11])[CH3:10].CO.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:7]([CH:3]([C:4](=[O:6])[CH3:5])[CH2:2][O:1][C:9](=[O:11])[CH3:10])[CH3:8]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 2702992-Ethyl-3-oxobutanolHCID 516892Sodium Bicarbonate

Produkt 1

HCID 10898964Acetic acid 2-ethyl-3-oxo-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

3-Hydroxymethyl-pentan-2-one (20.7 g) was dissolved in CHCl3 (150 mL) and cooled in an ice bath. Acetic anhydride (80 mL) was added, followed by DMAP (2.18 g), and the mixture was stirred overnight at room temperature. After cooling in an ice bath, MeOH (120 mL) was added dropwise, and the mixture was poured into a saturated aqueous NaHCO3 solution. After extraction with DCM twice, the combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to give 28.0 g of a light-yellow liquid. 1H NMR (400 MHz, CDCl3) δ 0.93 (t, J=8 Hz, 3H), 1.46-1.75 (m, 2H), 2.03 (s, 3H), 2.20 (s, 3H), 2.77 (quint., J=6.5 Hz, 1H), 4.20 (d, J=7 Hz, 3H).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. temperatureAfter cooling in an ice bath
  3. extractionAfter extraction with DCM twice
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-59cd7a8427e64aa59ace39ad6c78da57
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728018B2

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