Ethyl oxoacetate → Ethyl 3-cyclopropyl-2-hydroxy-propanoate

HRID 56660

Reaktionsgleichung

Reaktionsgleichung von HRID 56660
[O:1]=[CH:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[Mg][CH2:10][CH:11]1[CH2:13][CH2:12]1>C1COCC1.C(OCC)(=O)C>[CH:11]1([CH2:10][CH:2]([OH:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:13][CH2:12]1

Komponenten

5

Edukt 2

HCID 70211Ethyl oxoacetateHCID 178419657HCID 178419657, Verbindung

Produkt 1

HCID 116489250Ethyl 3-cyclopropyl-2-hydroxy-propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under argon and with ice cooling, a solution of 5.4 g (purity 50%, 26.7 mmol) of ethyl oxoacetate in 50 ml of THF was quickly added dropwise to 7.6 g (48 mmol, 1.8 eq.) of bromo(cyclopropylmethyl)magnesium. The reaction mixture was stirred for another 48 h, diluted with ethyl acetate and quenched with water. Celite was added, and the reaction mixture was stirred for 5 min and then filtered. After phase separation, the organic phase was washed once with water, dried (sodium sulphate), filtered and concentrated under reduced pressure. Yield: 2.6 g (60% of theory)

Aufarbeitung

  1. customquenched with water
  2. additionCelite was added
  3. stirringthe reaction mixture was stirred for 5 min
  4. filtrationfiltered
  5. customAfter phase separation
  6. washthe organic phase was washed once with water
  7. dry with materialdried (sodium sulphate)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-27e22d2fb738441eb0d64cce107c8a92
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434690B2

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