HCID 53669740, compound → HCID 70431619, compound

HRID 986548Notes

Reaction equation

HRID 986548 reaction equation
[C:1]([C:14]1[CH:25]=[CH:24][C:17]([CH:18]=[CH:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[H][H]>N1C=CC=CC=1.[Pd]>[CH:1](/[C:14]1[CH:15]=[CH:16][C:17]([CH:18]=[CH:19][C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=1)=[CH:2]/[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 53669740HCID 53669740, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70431619HCID 70431619, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

A solution of methyl 4-(1-tridecynyl)cinnamate (1.020 g, 3 mmole from Example 4) in pyridine (20 ml) was hydrogenated in the presence of 5% palladium on barium sulphate (24 mg) until 1 equivalent of hydrogen was absorbed. After removal of the catalyst by filtration the solvent was removed to give the alkene as a pale yellow solid. Recrystallization from methanol gave 885 mg (87%) of pure (Z) alkene of mp 60°-62° C. indentical with that of Example 15.

Workup

  1. customwas absorbed
  2. customAfter removal of the catalyst
  3. filtrationby filtration the solvent
  4. customwas removed

Sources & evidence

ORD record
ord-768e4f1d4002405086f9caa4da921de3
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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