Chloromethyl ethyl ether → HCID 12529074, compound

HRID 2397221Notes

Reaction equation

HRID 2397221 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6]([CH3:29])=[C:7]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH2:30]([O:32][CH2:33]Cl)[CH3:31]>O1CCCC1>[CH2:30]([O:32][CH2:33][N:5]1[C:6]([CH3:29])=[C:7]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]1[CH3:3])[CH3:31]

Participants

5

Reactant 3

HCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 282663Diethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Product 1

HCID 12529074HCID 12529074, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

In 5 ml. of anhydrous tetrahydrofuran was suspended 193 mg. of a 50% oil dispersion of sodium hydride and after adding to the mixture 7 ml of anhydrous tetrahydrofuran solution of 1 g. of diethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, the resultant mixture was stirred at room temperature for a while. The red-brown reaction product thus obtained was cooled to temperatures of from -40° C. to -50° C. and after adding thereto 5 ml. of anhydrous tetrahydrofuran solution of 380 mg. of ethoxymethyl chloride at the same temperature, the mixture was stirred for one hour and 45 minutes at the same temperature. By treating further the reaction product as in Example 1, 370 mg. of white crystals of diethyl 1-ethoxymethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate melting at 125° C. was obtained. The product was confirmed in the infrared absorption spectra and the nuclear magnetic resonance spectra to completely coincide with the presumed structure.

Workup

  1. customThe red-brown reaction product thus obtained
  2. temperaturewas cooled to temperatures of from -40° C. to -50° C.
  3. additionafter adding
  4. additionBy treating further the reaction product as in Example 1, 370 mg

Sources & evidence

ORD record
ord-a66fa8e568764ee29d4fba272be8c224
Source dataset
uspto-grants-1977_05
Patent number
US04021434

Reaction notes

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