HCID 12923297, Verbindung → HCID 12923329, Verbindung

HRID 972060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 972060
[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][C@@H:11]([CH3:18])[CH2:10][CH2:9][CH2:8][C@@H: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 12923329HCID 12923329, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1.104 g. (4.084 mmoles) of (3R,7R)-E-Ethyl 8tert. 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 temperature, 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-dimethyloctanoate 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-58259f18add541f3944917adfc147184
Quelldatensatz
uspto-grants-1979_07
Patentnummer
US04163021

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