Tetrahydrofuran → HCID 21437225, compound

HRID 2397225Notes

Reaction equation

HRID 2397225 reaction equation
[O:1]1[CH2:5]C[CH2:3][CH2:2]1.[N+:6]([C:9]1[CH:10]=[C:11]([CH:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([CH2:26][CH2:27][CH3:28])[NH:18][C:17]([CH2:29][CH2:30][CH3:31])=[C:16]2[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:12]=[CH:13][CH:14]=1)([O-:8])=[O:7].[H-].[Na+].ClCOCC>C(O)(=O)C>[CH2:2]([O:1][CH2:5][N:18]1[C:17]([CH2:29][CH2:30][CH3:31])=[C:16]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:15]([C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([N+:6]([O-:8])=[O:7])[CH:10]=2)[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]1[CH2:26][CH2:27][CH3:28])[CH3:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 21437195HCID 21437195, compound

Product 1

HCID 21437225HCID 21437225, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
-20 °C

Procedure

In 10 ml. of tetrahydrofuran was dissolved 0.5 g. of diethyl 4-(3-nitrophenyl)-2,6-dipropyl-1,4-dihydropyridine-3,5-dicarboxylate and after adding to the solution 0.2 g. of a 50% oil dispersion of sodium hydride, the mixture was stirred for 2 hours at room temperature. After cooling the mixture to -20° C., 0.5 ml. of chloromethoxyethane was added thereto and the mixture reacted for 1.5 hours at temperatures of from -20° C. to -10° C. After adding to the reaction product 0.5 ml. of glacial acetic acid and 20 ml. of water, the product was extracted three times each time with 5 ml. of ether at room temperature. The extracts were combined, washed with 5 ml. of saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and the ether was distilled away. The residue was subjected to a silica gel column chromatography, using a 10:1 benzene-acetone mixed solvent as an eluant, the effluent thus recovered was examined by a thin layer chromatography, and the effluent of the main fraction recovered was concentrated. By recrystallizing the residue formed from hexane, 0.4 g. of colorless acicular crystals of diethyl 1-ethoxymethyl-4-(3-nitrophenyl)-2,6-dipropyl-1,4-dihydropyridine-3,5-dicarboxylate melting at 109°-110° C. were obtained.

Workup

  1. customthe mixture reacted for 1.5 hours at temperatures of from -20° C. to -10° C
  2. extractionof water, the product was extracted three times each time with 5 ml
  3. customat room temperature
  4. washwashed with 5 ml
  5. dry with materialof saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate
  6. distillationthe ether was distilled away
  7. customthe effluent thus recovered
  8. customthe effluent of the main fraction recovered
  9. concentrationwas concentrated
  10. customBy recrystallizing the residue
  11. customformed from hexane, 0.4 g

Sources & evidence

ORD record
ord-dd17fcfc85d2454988ba549691014622
Source dataset
uspto-grants-1977_05
Patent number
US04021434

Reaction notes

Loading…