Methyl iodide → HCID 54519254, compound

HRID 890144Notes

Reaction equation

HRID 890144 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O:16][CH2:17][CH:18]=[CH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:15])=[C:12]([CH3:26])[NH:11][C:10]([CH3:27])=[C:9]2[C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:39]I>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O:16][CH2:17][CH:18]=[CH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:15])=[C:12]([CH3:26])[N:11]([CH3:39])[C:10]([CH3:27])=[C:9]2[C:28]([O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])=[O:29])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69590542HCID 69590542, compound

Product 1

HCID 54519254HCID 54519254, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

277 mg (0.53 mmol) of 5-(3-phenyl-2-propene-1-yl) 3-(2-trimethylsilylethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate was dissolved in N,N-dimethylformamide. 40 mg (1.0 mmol) of sodium hydride (60%, oily) was added to the obtained solution. Then 0.05 ml (0.8 mmol) of methyl iodide was added to the resultant mixture, and they were stirred at room temperature for 2 hours. N,N-dimethylformamide was evaporated under reduced pressure. Water was added to the residue. After the extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=3/1) to obtain the title compound.

Workup

  1. customN,N-dimethylformamide was evaporated under reduced pressure
  2. additionWater was added to the residue
  3. extractionAfter the extraction with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-6d79f315738345179fac9f9b924c3f92
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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