Potassium Hydroxide → 4,7-Dihydro-2H-4,7-ethanoisoindole

HRID 732324Notes

Reaction equation

HRID 732324 reaction equation
C(OC([C:6]1[NH:7][CH:8]=[C:9]2[C:14]=1[CH:13]1[CH2:15][CH2:16][CH:10]2[CH:11]=[CH:12]1)=O)C.[OH-].[K+]>C(O)CO>[CH:6]1[NH:7][CH:8]=[C:9]2[C:14]=1[CH:13]1[CH2:15][CH2:16][CH:10]2[CH:11]=[CH:12]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 121166594,7-Ethano-2H-isoindole-1-carboxylic acid, 4,7-dihydro-, ethyl ester

Product 1

HCID 140256694,7-Dihydro-2H-4,7-ethanoisoindoleYield 70.4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
175 °C

Procedure

A light-resistant reaction vessel equipped with a reflux condenser was charged with the ethyl-4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate (1.95 g, 9.6 mmol) obtained in Step 2, 100 ml of ethylene glycol and 2.0 g of potassium hydroxide. The vessel was then purged with nitrogen, and the mixture was stirred for 2 hours at 175° C. The reaction mixture was then cooled to room temperature, and poured into ice water. The resulting solution was extracted with chloroform, the extract was washed with saturated saline and the obtained organic layer was dried over anhydrous sodium sulfate. Concentration of the solution under reduced pressure then gave 4,7-dihydro-4,7-etano-2H-isoindole (0.98 g, yield 70.4%).

Workup

  1. customA light-resistant reaction vessel equipped with a reflux condenser
  2. customThe vessel was then purged with nitrogen
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. additionpoured into ice water
  5. extractionThe resulting solution was extracted with chloroform
  6. washthe extract was washed with saturated saline
  7. dry with materialthe obtained organic layer was dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-8656d33b3c964078b9e181429be2a02d
Source dataset
uspto-grants-2009_09
Patent number
US07586117B2

Reaction notes

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