2,​4-​Hexadien-​1-​ol → Methyl 2,4-hexadienyl 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 652425Notes

Reaction equation

HRID 652425 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:9]([C:20]([OH:22])=[O:21])=[C:8]([CH3:23])[NH:7][C:6]=1[CH3:24])=[O:4].[CH2:25](O)[CH:26]=[CH:27][CH:28]=[CH:29]C.[CH:32]1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClC(Cl)C>[N+:17]([C:13]1[CH:12]=[C:11]([CH:10]2[C:5]([C:3]([O:2][CH2:1][CH:25]=[CH:26][CH:27]=[CH:28][CH3:29])=[O:4])=[C:6]([CH3:24])[NH:7][C:8]([CH3:23])=[C:9]2[C:20]([O:22][CH3:32])=[O:21])[CH:16]=[CH:15][CH:14]=1)([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 81042,​4-​Hexadien-​1-​olHCID 10868DicyclohexylcarbodiimideHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester

Product 1

HCID 73185387Methyl 2,4-hexadienyl 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateYield 89.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

664 mg (2 mM) of 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5dicarboxylic acid 3-methyl ester, 206 mg (2.1 mM) of 2,4-hexadien-1-ol, 433 mg (2.1 mM) of dicyclohexylcarbodiimide and 257 mg (2.1 mM) of 4-dimethylaminopyridine were dissolved in 20 ml of dichloroethane, and refluxed for 2 hours. Insoluble matters were filtered off, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography, and 734 mg of methyl 2,4-hexadienyl 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate was obtained (yield 89%).

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationInsoluble matters were filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6eadf601465d4bc893157f887d993b93
Source dataset
uspto-grants-1987_06
Patent number
US04672068

Reaction notes

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