(1,1'-Biphenyl)-4-carboxaldehyde → 2-[1-biphenyl-4-yl-meth-(Z)-ylidene]-succinic acid 4-tert-butyl ester 1-methyl ester

HRID 70875

反応式

HRID 70875 の反応式
[CH3:1][O:2][C:3](=[O:32])[C:4](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[C:33]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:38]=[CH:37][C:36]([CH:39]=O)=[CH:35][CH:34]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:32])/[C:4](=[CH:39]\[C:36]1[CH:37]=[CH:38][C:33]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:34][CH:35]=1)/[CH2:5][C:6]([O:8][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:7]

参加物

4

反応物 2

HCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 110157884-Tert-butyl 1-methyl 2-(triphenylphosphoranylidene)succinate

生成物 1

HCID 684245312-[1-biphenyl-4-yl-meth-(Z)-ylidene]-succinic acid 4-tert-butyl ester 1-methyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Next, a mixture of 2-(triphenylphosphanylidene)-succinic acid 4-tert-butyl ester 1-methyl ester (700 mg, 1.561 mmol) and biphenyl-4-carboxaldehyde (278 mg, 1.419 mmol) in toluene (20 mL) is refluxed for 4 days. The solvent is removed under reduced pressure and the residue is purified by column chromatography using a gradient of 0-30% heptane/EtOAc to give 2-[1-biphenyl-4-yl-meth-(Z)-ylidene]-succinic acid 4-tert-butyl ester 1-methyl ester as an oil, 1H-NMR (400 MHz, CDCl3); δ ppm 1.47 (s, 9H), 3.52 (s, 2H), 3.84 (s, 3H), 7.37 (t, 1H), 7.46 (t, 4H), 7.62 (t, 4H), 7.89 (s, 1H).

後処理

  1. temperatureis refluxed for 4 days
  2. customThe solvent is removed under reduced pressure
  3. customthe residue is purified by column chromatography

出典と根拠

ORDレコード
ord-2d1c0ced42c54a25bc3b1cf352e8384e
出典データセット
uspto-grants-2014_09
特許番号
US08822534B2

関連ノート

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