HCID 12923297, Verbindung → HCID 86737845, Verbindung

HRID 1277539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1277539
[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, Verbindung

Produkt 1

HCID 86737845HCID 86737845, 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 temperature, for 2 hours during which time approximately one equivalent ofhydrogen 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-c6bafd84df1f4c88bee2ff79be3a04ca
Quelldatensatz
uspto-grants-1981_07
Patentnummer
US04277610

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