Chloromethyl Methyl Ether → HCID 86749474, compound

HRID 1683963Notes

Reaction equation

HRID 1683963 reaction equation
[H-].[Na+].[CH:3](=[C:10]1/[C:11](=[O:29])[NH:12][C:13](=[O:28])/[C:14]/1=[CH:15]/[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1)\[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:30][O:31][CH2:32]Cl>CN(C)C=O>[CH3:30][O:31][CH2:32][N:12]1[C:13](=[O:28])/[C:14](=[CH:15]/[C:16]2[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=2)/[C:10](=[CH:3]\[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)/[C:11]1=[O:29]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 6438903T 686

Product 1

HCID 86749474HCID 86749474, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 63.2% sodium hydride (0.38 g) in dimethylformamide (10 ml) is added dropwise a solution of (3E, 4E)-3-benzylidene-4-(3,4,5-trimethoxybenzylidene)-2,5-pyrrolidinedione (3.65 g)in dimethylformamide (10 ml) under ice-cooling, and the mixture is stirred at room temperature for one hour. To the mixture is added dropwise methoxymethyl chloride (0.84 ml) under ice-cooling, and the mixture is stirred at room temperature overnight. The mixture is evaporated to remove the solvent, and to the residue is added ethyl acetate. The mixture is washed, dried, and evaporated to remove the solvent. The resulting residue is purified by silica gel column chromatography (solvent; n-hexane:trichloromethane:ethyl acetate=5:5:4) to give (3E,4E)-1-methoxymethyl-3-benzylidene-4-(3,4,5-trimethoxybenzylidene)-2,5-pyrrolidinedione (3.0 g) as yellow crystals.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture is stirred at room temperature overnight
  4. customThe mixture is evaporated
  5. customto remove the solvent
  6. additionto the residue is added ethyl acetate
  7. washThe mixture is washed
  8. customdried
  9. customevaporated
  10. customto remove the solvent
  11. customThe resulting residue is purified by silica gel column chromatography (solvent; n-hexane:trichloromethane:ethyl acetate=5:5:4)

Sources & evidence

ORD record
ord-dd2654b31b724cf29e738b8d998a3f22
Source dataset
uspto-grants-1997_06
Patent number
US05639789

Reaction notes

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