Hydrochloric Acid → ethyl-4,9-dihydro-4,9-ethano-2H-benz[f]isoindole-1-carboxylate

HRID 10154

Reaktionsgleichung

C1(S([C:10]2[CH:11]3[CH2:21][CH2:20][CH:18]([CH:19]=2)[C:17]2[C:12]3=[CH:13][CH:14]=[CH:15][CH:16]=2)(=O)=O)C=CC=CC=1.[N+:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])#[C-:23].C(O[K])(C)(C)C.Cl>C1COCC1>[CH2:28]([O:27][C:25]([C:24]1[NH:22][CH:23]=[C:19]2[C:10]=1[CH:11]1[CH2:21][CH2:20][CH:18]2[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=21)=[O:26])[CH3:29]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Under an argon atmosphere, 0.296 g (1.0 mmol) of the obtained 1,4-dihydro-2-phenylsulfonyl-1,4-ethanonaphthalene, 0.13 ml (1.15 mmol) of ethyl isocyano-acetate and 30 ml of anhydrous THF were charged and cooled to 0° C. Into the mixture, 1.7 ml of tert-BuOK (1 M THF solution) was dropped over two hours and the resultant mixture was stirred for three hours at room temperature. After the completion of reaction, the reaction mixture was added with dilute hydrochloric acid, washed in turn with an aqueous saturated sodium bicarbonate solution, distilled water and saturated saline and dried with anhydrous sodium sulfate. The product was purified with silica gel column chromatography (chloroform) to obtain ethyl-4,9-dihydro-4,9-ethano-2H-benz[f]isoindole-1-carboxylate (0.243 g, yield: 91%).

Aufarbeitung

customAfter the completion of reaction
washwashed in turn with an aqueous saturated sodium bicarbonate solution
distillationdistilled water and saturated saline
dry with materialdried with anhydrous sodium sulfate
customThe product was purified with silica gel column chromatography (chloroform)

Quellen und Nachweise

ORD-Eintrag: ord-98a2d165b8174d258df596d366a29224
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07094625B2

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