5259-50-7 → HCID 67300624, compound

HRID 1015587Notes

Reaction equation

HRID 1015587 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH:9]2[CH2:11][CH2:12][C:6]1([O:13][CH3:14])[CH:7]=[CH:8]2)=[O:4]>[Pd].CO>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH:9]2[CH2:11][CH2:12][C:6]1([O:13][CH3:14])[CH2:7][CH2:8]2)=[O:4]

Participants

4

Reactant 1

HCID 27241515259-50-7

Product 1

HCID 67300624HCID 67300624, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a 100-mL, round-bottomed flask containing a magnetic stir bar were added 5% palladium/carbon catalyst (100 mg) and methanol (20 mL). Neat 1-methoxybicyclo[2.2.2]oct-5-ene-2-carboxylic acid methyl ester (1.96 g, 1.80 mL, 10.0 mmol) was added. A balloon containing H2 gas was attached and the mixture was stirred at room temperature overnight. The catalyst was removed by vacuum filtration through a small plug of silica gel and the solvent was removed under reduced pressure to provide the title compound. NMR (DMSO-d6, 300 MHz) δ 1.40-1.89 (m, 11H), 2.87 (ddd, J=10.5, 6.4, 2.0 Hz, 1H), 3.07 (s, 3H), 3.57 (s, 3H). MS (ESI+) m/z 200 (M+H)+.

Workup

  1. additionTo a 100-mL, round-bottomed flask containing a magnetic stir bar
  2. additionA balloon containing H2 gas
  3. customThe catalyst was removed by vacuum filtration through a small plug of silica gel
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-43ea1fdd7f1f432d9924b2009620b94b
Source dataset
uspto-grants-2011_07
Patent number
US07985768B2

Reaction notes

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