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

HRID 10154

반응식

HRID 10154 반응식
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]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 533707Ethyl isocyanoacetateHCID 219779221,4-Dihydro-2-phenylsulfony-1,4-ethanonaphthaleneHCID 178418922HCID 178418922, 화합물

생성물 1

HCID 72766033ethyl-4,9-dihydro-4,9-ethano-2H-benz[f]isoindole-1-carboxylate수율 91%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-98a2d165b8174d258df596d366a29224
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094625B2

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