Bicyclo[2.2.2]octa-2,5-diene-2-carboxylic acid → Bicyclo[2.2.2]oct-2-ene-2-carboxylic acid

HRID 8075Notes

Reaction equation

HRID 8075 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH:5]=[CH:6]1)[CH:3]=[C:2]2[C:9]([OH:11])=[O:10]>CCOC(C)=O.[Pd]>[CH:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]=[C:2]2[C:9]([OH:11])=[O:10]

Participants

4

Reactant 1

HCID 14423377Bicyclo[2.2.2]octa-2,5-diene-2-carboxylic acid

Product 1

HCID 22014830Bicyclo[2.2.2]oct-2-ene-2-carboxylic acidYield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Compound 11A (600 mg, 3.99 mmol) was dissolved in EtOAc (5 mL), 5% Pd/C (12 mg) was added and the mixture was stirred under a hydrogen balloon for 1.5 h. The reaction mixture was filtered through a pad of celite and concentrated under reduced pressure to give 600 mg of compound 11B as a yellow oil. No further purification was necessary. HPLC conditions: 95% at 2.65 min (YMC S5 ODS 4.6×50 mm, 10%-90% aqueous methanol over 4 minute gradient with 0.2% H3PO4, detecting at 220 nm). C. Bicyclo[2.2.2]oct-2-ene-2-carbonyl chloride (11C)

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8959462339fc4fa39d40a4aaa8d1a18d
Source dataset
uspto-grants-2006_08
Patent number
US07087636B2

Reaction notes

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