HCID 12923297, compound → HCID 12923328, compound

HRID 1763405Notes

Reaction equation

HRID 1763405 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][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]

Participants

5

Reactant 2

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

Product 1

HCID 12923328HCID 12923328, 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 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.).

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-c299b1c7e09444f6bc9e7a0935696266
Source dataset
uspto-grants-1978_09
Patent number
US04111961

Reaction notes

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