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

HRID 327602Notes

Reaction equation

HRID 327602 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-39c2c80f52ff45138b293983d532080e
Source dataset
uspto-grants-1993_12
Patent number
US05274002

Reaction notes

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