Tetrahydrofuran → HCID 70634419, compound

HRID 2397223Notes

Reaction equation

HRID 2397223 reaction equation
[O:1]1[CH2:5]C[CH2:3][CH2:2]1.[CH3:6][C:7]1[NH:8][C:9]([CH3:38])=[C:10]([C:30]([O:32][CH2:33][CH2:34][O:35][CH2:36][CH3:37])=[O:31])[CH:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:12]=1[C:13]([O:15][CH2:16][CH2:17][O:18][CH2:19][CH3:20])=[O:14].[H-].[Na+].ClCOCC>O.C(O)(=O)C>[CH2:2]([O:1][CH2:5][N:8]1[C:7]([CH3:6])=[C:12]([C:13]([O:15][CH2:16][CH2:17][O:18][CH2:19][CH3:20])=[O:14])[CH:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:10]([C:30]([O:32][CH2:33][CH2:34][O:35][CH2:36][CH3:37])=[O:31])=[C:9]1[CH3:38])[CH3:3]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 12706971HCID 12706971, compound

Product 1

HCID 70634419HCID 70634419, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In 20 ml. of anhydrous tetrahydrofuran was dissolved 10 g. of bis(2-ethoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4 -dihydropyridine-3,5-dicarboxylate and then the solution was added dropwise to 10 ml. of an anhydrous tetrahydrofuran suspension of 1.2 g. of a 50% oil dispersion of sodium hydride under stirring. After stirring the mixture further for 30 minutes at room temperature, the mixture was cooled to -10° C., 5 ml. of anhydrous tetrahydrofuran solution of 2.5 g. of chloromethoxyethane was added thereto over a period of 15 minutes, the temperature of the system was elevated gradually up to 0° C. over a period of about 15 minutes, and then the mixture was maintained at 0° C. for 15 minutes. The reaction product was cooled again to -10° C. and 2 ml. of acetic acid was added to the product. After stopping the cooling, 100 ml. of water was added to the product and then the product was extracted three times each time with 30 ml. of ether. The ether extracts were combined, dried over anhydrous sodium sulfate and then ether was distilled away. By recrystallizing the residue from 20:1 hexane-ethanol mixed solvent, 8.6 g. of colorless plate crystals of bis(2-ethoxyethyl) N-ethoxymethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate melting at 63°-63.5° C. were obtained.

Workup

  1. temperaturethe mixture was cooled to -10° C.
  2. waitover a period of 15 minutes
  3. waitthe temperature of the system was elevated gradually up to 0° C. over a period of about 15 minutes
  4. temperaturethe mixture was maintained at 0° C. for 15 minutes
  5. temperatureThe reaction product was cooled again to -10° C.
  6. extractionthe product was extracted three times each time with 30 ml
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationether was distilled away
  9. customBy recrystallizing the residue from 20:1 hexane-ethanol mixed solvent, 8.6 g

Sources & evidence

ORD record
ord-2f7548e8e17c467cbf16bd5964596f41
Source dataset
uspto-grants-1977_05
Patent number
US04021434

Reaction notes

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