HCID 67780109, compound → HCID 53803245, compound

HRID 327972Notes

Reaction equation

HRID 327972 reaction equation
[CH3:1][O:2][C:3](=[O:33])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[C:28]2[CH2:27][CH2:26][CH2:25][C:24](=[O:29])[C:23]=2[CH:22]=[CH:21][C:20]=1[CH2:30][CH:31]=[CH2:32].[H][H]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:33])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[C:28]2[CH2:27][CH2:26][CH2:25][C:24](=[O:29])[C:23]=2[CH:22]=[CH:21][C:20]=1[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 2

HCID 67780109HCID 67780109, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53803245HCID 53803245, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.72 g (3.84 mmol) of (E)-3-[2-[5-[(5-oxo-2-(2-propenyl)-5,6,7,8-tetrahydro-1-naphthalenyl)oxy]pentyloxy]phenyl]-2-propenoic acid methyl ester from the preceding experiment, 0.1 g of 10% palladium of carbon, and 50 mL of ethyl acetate was stirred in an atmosphere of hydrogen until gas uptake ceased. The catalyst was filtered with suction on a pad of Celite and the filter cake was washed thoroughly with ethyl acetate. Concentration of the combined filtrate and washes under reduced pressure gave a yellow oil which was chromatographed on 50 g of silica gel. Elution with 4:1 hexane-ether afforded 1.35 g (78%) of 2-[5-[(5-oxo-2-propyl-5,6,7,8-tetrahydro-1-naphthalenyl)oxy]pentyloxy]benzenepropanoic acid methyl ester as a pale-yellow oil.

Workup

  1. filtrationThe catalyst was filtered with suction on a pad of Celite
  2. washthe filter cake was washed thoroughly with ethyl acetate
  3. customConcentration of the combined filtrate and washes under reduced pressure gave a yellow oil which
  4. customwas chromatographed on 50 g of silica gel
  5. washElution with 4:1 hexane-ether

Sources & evidence

ORD record
ord-931386f9e86b48e8a40daa10c000a3d1
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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