Tetrahydrofuran → HCID 21437204, compound

HRID 2397226Notes

Reaction equation

HRID 2397226 reaction equation
[O:1]1[CH2:5]C[CH2:3][CH2:2]1.[C:6]([C:9]1[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:13]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:12]([CH3:29])[NH:11][C:10]=1[CH3:30])(=[O:8])[CH3:7].[H-].[Na+].ClCOCC>C1C=CC=CC=1.CC(C)=O.C(O)(=O)C>[C:6]([C:9]1[CH:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[C:13]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:12]([CH3:29])[N:11]([CH2:5][O:1][CH2:2][CH3:3])[C:10]=1[CH3:30])(=[O:8])[CH3:7]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydrideHCID 19823411HCID 19823411, compound

Product 1

HCID 21437204HCID 21437204, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 22015841Benzene methyl ketoneSolvent

Conditions

Temperature
-10 °C

Procedure

In 7 ml. of tetrahydrofuran was dissolved 0.5 g. of ethyl 3-acetyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine- 5-carboxylate and after adding to the solution 0.2 g. of a 50% oil dispersion of sodium hydride, the mixture was stirred for 30 minutes at room temperature. After cooling the mixture to -10° C., 0.5 ml. of chloromethoxyethane was added thereto, the temperature of the mixture was elevated to room temperature over a period of about 20 minutes, and after 15 minutes the mixture was cooled again to -10° C. Then, 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. The extracts were combined, washed with 5 ml. of saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then ether was distilled away. The residue formed was subjected to a silica gel column chromatography, using a 10:1 benzene-acetone mixed solvent as an eluant, the effluent was examined by a thin layer chromatography, and then the effluent of the main fraction was concentrated. By recrystallizing the residue thus obtained from a 10:1 benzene-hexane mixed solvent, 0.45 g. of faint yellow acicular crystals of ethyl 3-acetyl-1-ethoxymethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-5-carboxylate melting at 110°-111° C. were obtained.

Workup

  1. temperatureafter 15 minutes the mixture was cooled again to -10° C
  2. extractionof water, the product was extracted three times each time with 5 ml
  3. washwashed with 5 ml
  4. dry with materialof saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate
  5. distillationether was distilled away
  6. customThe residue formed
  7. concentrationthe effluent of the main fraction was concentrated
  8. customBy recrystallizing the residue
  9. customthus obtained from a 10:1 benzene-hexane mixed solvent, 0.45 g

Sources & evidence

ORD record
ord-4d9d9b83e8464b998620e04571aa0c2a
Source dataset
uspto-grants-1977_05
Patent number
US04021434

Reaction notes

Loading…