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 2191393ノート

反応式

HRID 2191393 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-b5d3d6ec95624d939ee608e838a375e7
出典データセット
uspto-grants-2012_12
特許番号
US08329682B2

反応ノート

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