Tetrahydrofuran → HCID 21437198, compound

HRID 2397228Notes

Reaction equation

HRID 2397228 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][C:7]1[NH:8][C:9]([CH3:32])=[C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[H-].[Na+].ClCOCC=C>C(O)(=O)C>[CH2:2]([O:1][CH2:5][N:8]1[C:9]([CH3:32])=[C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=2)[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:7]1[CH3:6])[CH:3]=[CH2:4]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 282663Diethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylateHCID 12400791Allyl chloromethyl ether

Product 1

HCID 21437198HCID 21437198, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
-10 °C

Procedure

In 10 ml. of tetrahydrofuran was dissolved 1.0 g. of diethyl 2,6-dimethyl-4-(3-nitrophenyl)-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 30 minutes at room temperature. After cooling the mixture to -10° C., 0.5 ml. of 3-chloromethoxy-1-propene was added thereto, the temperature was elevated to room temperature over a period of about 20 minutes, and then after 15 minutes the mixture was cooled again 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 then ether was distilled away. The residue was subjected to a silica gel column chromatography using benzene as an eluant. The effluent was then subjected to a thin layer chromatography, and then the effluent or the main fraction was concentrated to provide a white crystalline material. By recrystallizing the crystals from benzene-hexane, 0.74 g. of diethyl 1-allyloxymethyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate melting at 111°-112° 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. customat room temperature
  4. washwashed with 5 ml
  5. dry with materialof saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate
  6. distillationether was distilled away
  7. concentrationthe effluent or the main fraction was concentrated
  8. customto provide a white crystalline material
  9. customBy recrystallizing the crystals from benzene-hexane, 0.74 g

Sources & evidence

ORD record
ord-700bb8ab1e5640c39e4e20b17b34e182
Source dataset
uspto-grants-1977_05
Patent number
US04021434

Reaction notes

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