HCID 12923297, compound → HCID 12923329, compound

HRID 427127Notes

Reaction equation

HRID 427127 reaction equation
[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]

Participants

5

Reactant 2

HCID 12923297HCID 12923297, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 12923329HCID 12923329, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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 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.).

Workup

  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

Sources & evidence

ORD record
ord-d514191bd71642aa82ff5f06280ab815
Source dataset
uspto-grants-1979_10
Patent number
US04172958

Reaction notes

Loading…