HCID 20306565, compound → HCID 70583183, compound

HRID 46547Notes

Reaction equation

HRID 46547 reaction equation
[C:1]([O:5][C:6]([C:8]1([CH2:19][C:20]#[C:21][CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10][CH:9]1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCCCCC.CC(C)=O.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[C:1]([O:5][C:6]([C:8]1([CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10][CH:9]1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 20306565HCID 20306565, compound2×

Product 1

HCID 70583183HCID 70583183, compound

Reagents, catalysts & solvents 3

HCID 131709914Lindlars catalystCatalystHCID 180AcetoneSolventHCID 8058HexaneSolvent

Procedure

A 690 mg quantity of 5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (compound (2-a)) is dissolved in a mixture of 5 ml of n-hexane and 5 ml of acetone and reduced at room temperature and atmospheric pressure with addition of 3.2 g of a Lindlar catalyst. The catalyst is filtered off from the reaction mixture, and the solvent distilled off. The residue is purified by a silica gel column and distilled in a vacuum, giving 5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone (compound (2-b), R1 =t-Bu, R2 =CH3) in a yield of 99.8%, b.p. 81-84° C./0.005 mm Hg.

Workup

  1. customreduced at room temperature
  2. filtrationThe catalyst is filtered off from the reaction mixture
  3. distillationthe solvent distilled off
  4. customThe residue is purified by a silica gel column
  5. distillationdistilled in a vacuum

Sources & evidence

ORD record
ord-9104ffd3df934580ab5c4d700b7616f6
Source dataset
uspto-grants-1979_11
Patent number
US04173707

Reaction notes

Loading…