Hydrochloric Acid → 4,7-Ethano-2H-isoindole-1-carboxylic acid, 4,7-dihydro-, ethyl ester

HRID 746982

Reaktionsgleichung

Reaktionsgleichung von HRID 746982
C1(S([CH:10]2[CH:15](S(C3C=CC=CC=3)(=O)=O)[CH:14]3[CH2:25][CH2:26][CH:11]2[CH:12]=[CH:13]3)(=O)=O)C=CC=CC=1.[N+:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])#[C-:28].CC(C)([O-])C.[K+].Cl>O1CCCC1>[CH2:33]([O:32][C:30]([C:29]1[NH:27][CH:28]=[C:15]2[C:10]=1[CH:11]1[CH2:26][CH2:25][CH:14]2[CH:13]=[CH:12]1)=[O:31])[CH3:34]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 533707Ethyl isocyanoacetateHCID 127784115,6-Di(benzenesulfonyl)bicyclo[2.2.2]oct-2-eneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 121166594,7-Ethano-2H-isoindole-1-carboxylic acid, 4,7-dihydro-, ethyl esterAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A reaction system of a mixed solution of 7.76 g (20 mmol) of the resultant 5,6-bis(phenylsulfonyl)-bicyclo[2,2,2]octa-2-ene and 50 ml of anhydrous tetrahydrofuran was replaced with nitrogen. Then, 2.425 ml (22 mmol) of ethyl isocyanoacetate were added to the mixed solution, and the whole was cooled to 0° C. Potassium tert-butoxide (50 ml/l M THF solution) was dropped into the mixture in 2 hours, and the whole was stirred at room temperature for 3 hours. After the completion of the reaction, diluted hydrochloric acid was added to the reaction mixture. Then, the reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate, distilled water, and a saturated salt solution in this order, and was dried with anhydrous sodium sulfate. The dried product was purified by means of silica gel column chromatography (chloroform) to yield ethyl-4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate (3.5 g, 16 mmol, 80% yield).

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. washThen, the reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. distillationdistilled water
  4. dry with materiala saturated salt solution in this order, and was dried with anhydrous sodium sulfate
  5. customThe dried product was purified by means of silica gel column chromatography (chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-d119dedd11024b2fb9cd6846addc1f2a
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07394096B2

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