Ethyl Acetoacetate → ethyl (3R)-3-hydroxybutanoate

HRID 530274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530274
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]>CO>[OH:4][C@H:3]([CH3:5])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6]

Komponenten

3

Edukt 1

HCID 8868Ethyl Acetoacetate

Produkt 1

HCID 440030ethyl (3R)-3-hydroxybutanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Ethyl acetoacetate (7.5 g) and dry methanol (25 mL) were mixed and deoxygenated with flowing nitrogen for five minutes. The catalyst [(R)—Ru(BINAP)Cl2]2NEt3 (0.1 mol %) was added along with 2N HCl (0.1 mol %). The mixture was transferred to a standard Parr reactor apparatus and flushed by evacuating and refilling with hydrogen several times. The apparatus was heated at 50° C. with stirring under 100 psi of hydrogen for 16 h. After completion of reaction (monitored by TLC) the reaction was cooled and concentrated under reduced pressure. The residue was subjected to column chromatographic purification with petroleum ether/ethyl acetate (9:1 v/v) to get pure (R)-alcohol 43 as a colorless liquid.

Aufarbeitung

  1. customdeoxygenated with flowing nitrogen for five minutes
  2. additionThe catalyst [(R)—Ru(BINAP)Cl2]2NEt3 (0.1 mol %) was added along with 2N HCl (0.1 mol %)
  3. customflushed
  4. customby evacuating
  5. customAfter completion of reaction (monitored by TLC) the reaction
  6. temperaturewas cooled
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was subjected to column chromatographic purification with petroleum ether/ethyl acetate (9:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-d15ce573f601488c9b6b67f4a2a73d3e
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353077B2

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