Methanol → Dimethyl 2,5-dimethyl-4-[2-(2-trimethylsilylethenyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate

HRID 279865Notes

Reaction equation

HRID 279865 reaction equation
[CH3:1][Si:2]([CH3:14])([CH3:13])[CH:3]=[CH:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O.[NH2:15]/[C:16](/[CH3:22])=[CH:17]\[C:18]([O:20][CH3:21])=[O:19].[C:23]([O:29][CH3:30])(=[O:28])[CH2:24][C:25](C)=O.[CH3:31]O>>[CH3:22][C:16]1[NH:15][CH2:25][C:24]([CH3:31])([C:23]([O:29][CH3:30])=[O:28])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[CH:4]=[CH:3][Si:2]([CH3:14])([CH3:13])[CH3:1])[C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 4

HCID 887MethanolHCID 7757Methyl acetoacetateHCID 643918Methyl 3-aminocrotonateHCID 543012002-(2-Trimethylsilylethenyl)benzaldehyde

Product 1

HCID 74031287Dimethyl 2,5-dimethyl-4-[2-(2-trimethylsilylethenyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate

Procedure

To the Compound 1a (3.1 mmol) in anhydrous methanol (8 ml) was added methyl 3-aminocrotonate (3.1 mmol) and methyl acetoacetate (3.1 mmol) and the resulting solution heated at reflux under nitrogen for 5 days. The solvent was removed in vacuo to yield a yellow oil which was purified by flash chromatography on silica gel eluted with hexane:diethyl ether (1:1) to afford Compound 1b as yellowish powder (Rf =0.3, m.p. 148°-150° C.).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux under nitrogen for 5 days
  3. customThe solvent was removed in vacuo
  4. customto yield a yellow oil which
  5. customwas purified by flash chromatography on silica gel
  6. washeluted with hexane:diethyl ether (1:1)

Sources & evidence

ORD record
ord-96e60ece598b4b6fa5ed4d7b8e3d9461
Source dataset
uspto-grants-1986_05
Patent number
US04587253

Reaction notes

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