Methyl acetoacetate → HCID 13883017, compound

HRID 652007Notes

Reaction equation

HRID 652007 reaction equation
[CH3:1][O:2][CH:3]([O:13][CH3:14])[CH2:4][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]([CH3:27])=O>CO>[CH3:22][C:16]1[NH:15][C:25]([CH3:27])=[C:24]([C:23]([O:29][CH3:30])=[O:28])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[CH2:4][CH:3]([O:13][CH3:14])[O:2][CH3:1])[C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 643918Methyl 3-aminocrotonateHCID 138830162-(2,2-Dimethoxyethyl)benzaldehyde

Product 1

HCID 13883017HCID 13883017, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.5 grams (0.013 mole) of 2-(2,2-dimethoxyethyl)benzaldehyde in 25 milliliters of dry methanol was added 1.48 grams (0.013 mole) of methyl 3-aminocrotonate and 1.49 grams (0.013 mole) of methyl acetoacetate and the resulting mixture was heated at reflux temperature for 3 days. At the end of this time, the solvent was removed on the rotary evaporator and the residue purified by flash chromatography on silica gel (250-400 mesh) using 2 percent methanol in chloroform as eluant to obtain 2.11 grams (42 percent yield) dimethyl 2,6-dimethyl-4-[2-(2,2-dimethoxyethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate intermediate (Rf 0.3) as a white solid, m.p. 113°-114° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux temperature for 3 days
  3. customAt the end of this time, the solvent was removed on the rotary evaporator
  4. customthe residue purified by flash chromatography on silica gel (250-400 mesh)

Sources & evidence

ORD record
ord-7f01e597260846c1b6549e35420ca613
Source dataset
uspto-grants-1987_06
Patent number
US04670443

Reaction notes

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