Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 2-O-tert-butyl 4-O-ethyl 5-(3-ethoxy-3-oxoprop-1-enyl)-3-methyl-1H-pyrrole-2,4-dicarboxylate

HRID 2191393노트

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HRID 2191393 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:20])=[C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:9][C:10]=1[CH:11]=O)=[O:5])[CH3:2].[CH2:21]([O:23][C:24]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:25])[CH3:22]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:20])=[C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[NH:9][C:10]=1[CH:11]=[CH:26][C:24]([O:23][CH2:21][CH3:22])=[O:25])=[O:5])[CH3:2]

참가 물질

6

반응물 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 98142842-O-tert-butyl 4-O-ethyl 5-formyl-3-methyl-1H-pyrrole-2,4-dicarboxylate

생성물 1

HCID 685279692-O-tert-butyl 4-O-ethyl 5-(3-ethoxy-3-oxoprop-1-enyl)-3-methyl-1H-pyrrole-2,4-dicarboxylate수율 84%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

5-Formyl-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1 b (23 g, 81.7 mmol) and (ethoxycarbonylmethylene)triphenylphosphorane (34.66 g, 99.4 mmol) were dissolved in 450 ml of tetrahydrofuran, and stirred at room temperature overnight under an argon atmosphere. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was concentrated under reduced pressure to obtain a yellow oil. The residue was dissolved in the solvent mixture of n-hexane and ethyl acetate (V:V=20:1), and purified by sand funnel decompression column chromatography to obtain the title compound 5-(2-ethoxycarbonyl-vinyl)-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1c (24 g, yield 84%) as a light yellow solid.

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto obtain a yellow oil
  3. custompurified by sand funnel decompression column chromatography

출처 및 근거

ORD 기록
ord-b5d3d6ec95624d939ee608e838a375e7
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329682B2

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