HCID 15052474, compound → HCID 15052478, compound

HRID 327604Notes

Reaction equation

HRID 327604 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9](/[CH:15]=[CH:16]/[CH:17]=[CH:18]/[CH:19]=[CH:20]/[CH:21]=[CH:22]/[C:23]([O:25][CH3:26])=[O:24])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[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 15052474HCID 15052474, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15052478HCID 15052478, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.22 g (0.62 mmol) of methyl 9-(3-cyclopentoxy-4-methoxyphenyl)-2,4,6,8-E,E,E,E-nontetraenoate in 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 20.9 hours 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 5% ethyl acetate in hexane. The final product is dried in vacuo and is found to be 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-c2b507cffb9c465db198b1f8880c2c11
Source dataset
uspto-grants-1993_12
Patent number
US05274002

Reaction notes

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