Ethane, 1-chloro-1-ethoxy- → HCID 21437191, compound

HRID 2397222Notes

Reaction equation

HRID 2397222 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:27])=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[H-].[Na+].Cl[CH:31]([O:33][CH2:34][CH3:35])[CH3:32]>O1CCCC1>[CH2:31]([O:33][CH:34]([N:3]1[C:4]([CH3:27])=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:2]1[CH3:1])[CH3:35])[CH3:32]

Participants

5

Reactant 3

HCID 23478Ethane, 1-chloro-1-ethoxy-HCID 24758Sodium hydrideHCID 282663Diethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 21437191HCID 21437191, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

In 50 ml. of anhydrous tetrahydrofuran was dissolved 5 g. of diethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine 3,5-dicarboxylate in a nitrogen gas stream and after adding to the solution 1 g. of a 50% oil dispersion of sodium hydride, the mixture was maintained at room temperature for 10 minutes. Then, 3 ml. of 1-chloro-1-ethoxyethane was added to the mixture under cooling to -40° C. and after removing the cooling bath, the resultant mixture was stirred for 30 minutes. After the reaction was over, 1 ml. of glacial acetic acid was added to the product and then the product was diluted with ethyl acetate. The reaction product was washed with water, saturated aqueous sodium bicarbonate solution, and then water, dried over anhydrous magnesium sulfate, and then the solvent was distilled away under a reduced pressure to provide crude diethyl N-(1-ethoxyethyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate. By purifying the product by means of a silica gel column chromatography and by using a 20:1 benzeneethyl acetate mixed solvent, 1 g. of faint-yellow oily diethyl N-(1-ethoxyethyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate was obtained. The product was confirmed in the infrared absorption spectra, the nuclear magnetic responance spectra, and the mass analysis spectra to completely coincide with the presumed structure.

Workup

  1. customafter removing the cooling bath
  2. additionof glacial acetic acid was added to the product
  3. additionthe product was diluted with ethyl acetate
  4. washThe reaction product was washed with water, saturated aqueous sodium bicarbonate solution
  5. dry with materialwater, dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under a reduced pressure
  7. customto provide crude diethyl N-(1-ethoxyethyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  8. customBy purifying the product by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-f6df88c52c8b48f2b85a67a00c6e789f
Source dataset
uspto-grants-1977_05
Patent number
US04021434

Reaction notes

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