methyl 5-(3-cyclopentoxy-4-methoxyphenyl)-2,4-E,E-pentadienoate → Methyl 5-(3-cyclopentoxy-4-methoxyphenyl)-n-pentanoate

HRID 1073746Notes

Reaction equation

HRID 1073746 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9](/[CH:15]=[CH:16]/[CH:17]=[CH:18]/[C:19]([O:21][CH3:22])=[O:20])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[Pd].CO>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 15052472methyl 5-(3-cyclopentoxy-4-methoxyphenyl)-2,4-E,E-pentadienoateHCID 178418361HCID 178418361, compound

Product 1

HCID 15052476Methyl 5-(3-cyclopentoxy-4-methoxyphenyl)-n-pentanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.20 g (0.66 mmol) of methyl 5-(3-cyclopentoxy-4-methoxyphenyl)-2,4-E,E-pentadienoate 75 mL of methanol is added 0.05 g of 5% palladium on carbon black. The suspension is shaken under a 50 psi atmosphere of hydrogen for 52 minutes after which time the excess gas is dissociated and the solution is filtered over Celite 545. The mixture is concentrated to dryness followed by liquid chromatography of the crude product over 100 g of silica gel eluting with 7.5% ethyl acetate in hexane. The final product is dried in vacuo and is found to be as analytically pure as an oil.

Workup

  1. filtrationthe solution is filtered over Celite 545
  2. concentrationThe mixture is concentrated to dryness
  3. dry with materialThe final product is dried in vacuo

Sources & evidence

ORD record
ord-052ef960ae4c4a2abba7c154de22c701
Source dataset
uspto-grants-1990_11
Patent number
US04971959

Reaction notes

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