HCID 12923297, Verbindung → HCID 12923328, Verbindung

HRID 1763405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1763405
[C:1]([O:5][CH2:6][C@H:7]([CH3:19])[CH2:8]/[CH:9]=[CH:10]/[C@H:11]([CH3:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Ni].C(OCC)(=O)C>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][CH:11]([CH3:18])[CH2:10][CH2:9][CH2:8][CH:7]([CH3:19])[CH2:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:17]

Komponenten

5

Edukt 2

HCID 12923297HCID 12923297, VerbindungHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 12923328HCID 12923328, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1.104 g. (4.084 mmoles) of (3R,7R)-E-Ethyl 8-tert. butoxy-3,7-dimethyl-4-octenoate, a small amount of Raney nickel, and 30 ml. of ethyl acetate was stirred in an atmosphere of hydrogen, at room temperture, for 2 hours during which time approximately one equivalent of hydrogen was taken up. The catalyst was filtered off and washed with ethyl acetate. Concentration of the combined filtrate and washes in vacuo followed by evaporative distillation afforded 1.045 g. (95%) of saturated ester (3S,7R)-Ethyl 8-tert. butoxy-3,7-dimethyloloctanoate as a colorless oil, b.p. 80°-83° C. (bath temperature) (0.15 mm Hg.).

Aufarbeitung

  1. additionA mixture of 1.104 g
  2. filtrationThe catalyst was filtered off
  3. washwashed with ethyl acetate
  4. distillationConcentration of the combined filtrate and washes in vacuo followed by evaporative distillation
  5. customafforded 1.045 g

Quellen und Nachweise

ORD-Eintrag
ord-c299b1c7e09444f6bc9e7a0935696266
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04111961

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