tert-Butanol → Tert-butyl 2,4-hexadienyl 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 652427ノート

反応式

HRID 652427 の反応式
[CH2:1]([O:7][C:8]([C:10]1[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:14]([C:25]([OH:27])=[O:26])=[C:13]([CH3:28])[NH:12][C:11]=1[CH3:29])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH3:6].[C:30](O)([CH3:33])([CH3:32])[CH3:31].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClC(Cl)C>[N+:22]([C:18]1[CH:17]=[C:16]([CH:15]2[C:10]([C:8]([O:7][CH2:1][CH:2]=[CH:3][CH:4]=[CH:5][CH3:6])=[O:9])=[C:11]([CH3:29])[NH:12][C:13]([CH3:28])=[C:14]2[C:25]([O:27][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:26])[CH:21]=[CH:20][CH:19]=1)([O-:24])=[O:23]

参加物

6

反応物 3

HCID 6386tert-ButanolHCID 10868DicyclohexylcarbodiimideHCID 727405614-(3-Nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid mono (2,4-hexadienyl) ester

生成物 1

HCID 73189303Tert-butyl 2,4-hexadienyl 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate収率 73.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 63651,1-Dichloroethane溶媒

実験手順

199 mg (0.5 mM) of 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid mono (2,4-hexadienyl) ester, 44 mg (0.6 mM) of tert-butanol, 113 mg (0.55 mM) of dicyclohexylcarbodiimide and 61 mg (0.5 mM) of 4-dimethylaminopyridine were dissolved in 5 ml of dichloroethane, and refluxed for 2 hours. After the reaction mixture was chilled, insoluble matters were filtered off. The solvent was evaporated under reduced pressure, and the residue was purified by silicas gel column chromatography to obtain 198 mg of a crude material. This material was recrystallized with methanol, and 166 mg of tert-butyl 2,4-hexadienyl 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate was obtained (yield 73%).

後処理

  1. temperaturerefluxed for 2 hours
  2. temperatureAfter the reaction mixture was chilled
  3. filtrationinsoluble matters were filtered off
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silicas gel column chromatography
  6. customto obtain 198 mg of a crude material
  7. customThis material was recrystallized with methanol

出典と根拠

ORDレコード
ord-04e3f2ab8c0246c98eb0cd575d3ba630
出典データセット
uspto-grants-1987_06
特許番号
US04672068

反応ノート

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