HCID 68524499, compound → HCID 59451682, compound

HRID 2386193Notes

Reaction equation

HRID 2386193 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:6]=[CH:7][CH:8]=1>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 68524499HCID 68524499, compound

Product 1

HCID 59451682HCID 59451682, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

After careful purging with argon and still under an atmosphere of argon, 10% palladium on carbon (0.015 g, 0.015 mmol) was suspended in 8 mL ethanol. 7-(3-methoxyphenyl)hept-6-enoic acid (2) was dissolved in 2 mL warm ethanol and injected into the reaction solution and stirring was commenced. The reaction vessel was then purged with hydrogen gas after which a hydrogen balloon was utilized to maintain a hydrogen atmosphere in the reaction vessel while stirring continued for 18 hours. The 10% palladium on carbon was filtered off on diatomaceous earth and the ethanolic filtrate collected and condensed in vacuo to provide the desired product in 93% yield (0.159 g) as a light yellow oil without further purification: 1H NMR (500 MHz, CDCl3) δ 7.24 (q, 1H), 6.79 (q, 3H), 3.83 (s, 3H), 2.63 (t, 2H), 2.39 (t, 3H), 1.69 (m, 4H), 1.41 (m, 4H); 13C NMR (500 MHz, CDCl3) δ 180.48, 159.62, 144.33, 129.24, 120.90, 114.23, 110.93, 100.01, 55.11, 35.96, 34.13, 31.19, 28.94, 24.64.

Workup

  1. customThe reaction vessel was then purged with hydrogen gas after which a hydrogen balloon
  2. temperatureto maintain a hydrogen atmosphere in the reaction vessel
  3. stirringwhile stirring
  4. filtrationThe 10% palladium on carbon was filtered off on diatomaceous earth
  5. customthe ethanolic filtrate collected
  6. customcondensed in vacuo

Sources & evidence

ORD record
ord-1a58d0c8d53447008bf910ad741f2d09
Source dataset
uspto-grants-2012_09
Patent number
US08268817B2

Reaction notes

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