Cyclohexene → 1-Oxo-1-furyl-7-methoxycarbony-cis-4-heptene

HRID 1613001Notes

Reaction equation

HRID 1613001 reaction equation
[O:1]=[C:2]([C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)[CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10].C1CCCCC=1>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C1(C)C=CC=CC=1>[O:1]=[C:2]([C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)[CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 110208121-Oxo-1-furyl-7-methoxycarbonyl-4-heptyne

Product 1

HCID 677897581-Oxo-1-furyl-7-methoxycarbony-cis-4-hepteneYield 90.6%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 1-oxo-1-furyl-7-methoxycarbonyl-4-heptyne [VII-1] (3.0 g) obtained in Example 13, a Lindlar catalyst (5% Pd-CaCO3 -PbO) (30 mg), cyclohexene (5.26 g) and toluene (12 ml) is charged in an atmospheric hydrogenation apparatus and subjected to reduction at room temperature under atmospheric pressure. After completion of the reaction, the catalyst is removed by filtration and the filtrate is concentrated to give 1-oxo-1-furyl-7-methoxycarbony-cis-4-heptene [VII-2] (2.74 g, yield; 90.4%).

Workup

  1. customobtained in Example 13
  2. customsubjected to reduction at room temperature under atmospheric pressure
  3. customAfter completion of the reaction
  4. customthe catalyst is removed by filtration
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-775dc62dee1c4e48a17d380c781704df
Source dataset
uspto-grants-1993_03
Patent number
US05191109

Reaction notes

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