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

HRID 909994Notes

Reaction equation

HRID 909994 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-].[Na+]>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 14798Sodium 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

Fed into a light-shielded reaction vessel equipped with a reflux condenser were 1.95 g (9.6 mmol) of ethyl-4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate synthesized in Step 1-2, 100 ml of ethylene glycol, and 2.0 g of sodium hydroxide. Then, the vessel was replaced with nitrogen and the mixture was stirred at 175° C. for 2 hours. After that, the reaction solution cooled to room temperature was poured into ice water, the whole was extracted with chloroform, and the extract was washed with a saturated salt solution. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to yield 4,7-dihydro-4,7-ethano-2H-isoindole (0.98 g, 70.4% yield).

Workup

  1. customFed into a light-shielded reaction vessel equipped with a reflux condenser
  2. temperatureAfter that, the reaction solution cooled to room temperature
  3. extractionthe whole was extracted with chloroform
  4. washthe extract was washed with a saturated salt solution
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70edd3e6801c4d928538720e0060182a
Source dataset
uspto-grants-2011_09
Patent number
US08021915B2

Reaction notes

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