2,3-Dichlorobenzaldehyde → 5-Cyclopentyl 3-methyl 4-(2,3-dichlorophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate

HRID 1789010ノート

反応式

HRID 1789010 の反応式
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:11][CH2:12][C:13](=O)[CH2:14][C:15]([O:17][CH3:18])=[O:16].[NH2:20][C:21]([CH3:31])=[CH:22][C:23]([O:25][CH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:24]>C(OCC)(=O)C>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]1[C:22]([C:23]([O:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:24])=[C:21]([CH3:31])[NH:20][C:13]([CH2:12][F:11])=[C:14]1[C:15]([O:17][CH3:18])=[O:16]

参加物

5

反応物 3

HCID 357452,3-DichlorobenzaldehydeHCID 14170515Methyl 4-fluoro-3-oxobutanoateHCID 66992092Cyclopentyl 3-aminobut-2-enoate

生成物 1

HCID 700905275-Cyclopentyl 3-methyl 4-(2,3-dichlorophenyl)-2-(fluoromethyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate収率 28.6%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

2,3-Dichlorobenzaldehyde (1.31 g, 7.5 mmoles), methyl 4-fluoro-3-oxobutanoate (1.0 g, 7.5 mmoles) and cyclopentyl 3-amino-2-butenoate (1.26 g, 7.5 mmoles) were heated at 90° with stirring under nitrogen for 2.5 hours. The reaction mixture was dissolved in ethyl acetate, dried (MgSO4) and the solvent was removed in vacuo. The residue was chromatographed on silica eluting with ethyl acetate/methylene chloride mixtures. The title compound (0.95 g) was obtained after crystallisation from petroleum ether (60°-80) mp 148°-50°.

後処理

  1. dry with materialdried (MgSO4)
  2. customthe solvent was removed in vacuo
  3. customThe residue was chromatographed on silica eluting with ethyl acetate/methylene chloride mixtures

出典と根拠

ORDレコード
ord-5099b83648494d408f4009e510dc0900
出典データセット
uspto-grants-1987_08
特許番号
US04686217

反応ノート

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