Ethanol → Ethyl 3-(4-chlorophenyl)-1H-pyrrole-2-carboxylate

HRID 623723노트

반응식

HRID 623723 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/S(C2C=CC(C)=CC=2)(=O)=O)=[CH:6][CH:5]=1.[N+:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])#[C-:23].CCO>C1COCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:23][NH:22][C:24]=2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 533707Ethyl isocyanoacetateHCID 10979228(E)-1-Chloro-4-(2-tosylvinyl)benzene

생성물 1

HCID 79327547Ethyl 3-(4-chlorophenyl)-1H-pyrrole-2-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Under N2, at 0° C. 60% NaH in mineral oil (3.11 g, 78 mmol) was added to a solution of (E)-1-chloro-4-(2-tosylvinyl)benzene (19 g, 64.9 mmol) in dry THF (300 mL). After 5 minutes ethyl 2-isocyanoacetate (7.76 mL, 71.4 mmol) was added and the reaction mixture stirred at room temperature. After 18 h EtOH (50 mL) was added and the solvents were evaporated under reduced pressure. The residue was partitioned between EtOAc (400 mL) and H2O (400 mL). The organic phase was washed with (100 mL), dried over Na2SO4, filtered and evaporated to dryness under reduced pressure. The crude product (16.55 g, “102%”) was used in the next step.

후처리

  1. customat 0° C
  2. customthe solvents were evaporated under reduced pressure
  3. customThe residue was partitioned between EtOAc (400 mL) and H2O (400 mL)
  4. washThe organic phase was washed with (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-17ef1a45d9f04beface7019ce7fc451d
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302988B2

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