Sodium hydride → methyl 3-(4-nitrophenyl)-1H-pyrrole-2-carboxylate

HRID 227667

반응식

HRID 227667 반응식
[H-].[Na+].CC1C=CC(S(/[CH:13]=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)(=O)=O)=CC=1.[N+:24]([CH2:26][C:27]([O:29][CH3:30])=[O:28])#[C-:25]>O1CCCC1.O.C(OCC)(=O)C>[N+:21]([C:18]1[CH:17]=[CH:16][C:15]([C:14]2[CH:13]=[CH:25][NH:24][C:26]=2[C:27]([O:29][CH3:30])=[O:28])=[CH:20][CH:19]=1)([O-:23])=[O:22]

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 547815Methyl isocyanoacetateHCID 138738071-methyl-4-[(1E)-2-(4-nitrophenyl)ethenesulfonyl]benzene

생성물 1

HCID 18616331methyl 3-(4-nitrophenyl)-1H-pyrrole-2-carboxylate수율 111.2%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
20 °C

실험 절차

To a suspension of 1.62 g (40.63 mmol) of 60% sodium hydride in mineral oil in 100 cm3 of tetrahydrofuran is added dropwise over 25 minutes, at a temperature in the region of 20° C. under an argon atmosphere, a mixture of 5.87 g (19.35 mmol) of 1-[(E)-2-(4-methylphenyl)sulfonylvinyl]-4-nitrobenzene and 3.7 cm3 (38.7 mmol) of methyl isocyanoacetate dissolved in 150 cm3 of tetrahydrofuran. After stirring for 5 hours at a temperature in the region of 20° C., the reaction mixture is taken up in a mixture of 100 cm3 of water and 200 cm3 of ethyl acetate. The organic phase is washed with twice 100 cm3 of water and 150 cm3 of saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 5.3 g of a brown oil, which is purified by flash chromatography [eluent: dichloromethane]. After concentrating the fractions under reduced pressure, 2.12 g of methyl 3-(4-nitrophenyl)-1H-pyrrole-2-carboxylate are obtained in the form of a yellow solid; M.W.=246, IE: m/z=246 M+, m/z=214 [M-CH3OH]+.

후처리

  1. additionis added dropwise over 25 minutes, at a temperature in the region of 20° C. under an argon atmosphere
  2. washThe organic phase is washed with twice 100 cm3 of water and 150 cm3 of saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

출처 및 근거

ORD 기록
ord-3da4cccee92f4a889bcf7673128033c1
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560571B2

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