Water → HCID 20026687, compound

HRID 1723065Notes

Reaction equation

HRID 1723065 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][C:5]1([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[O:9][CH:8]([CH2:10]Cl)[CH2:7][O:6]1.[CH3:23][O-:24].[Na+].[I-].[Na+].O>CS(C)=O>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][C:5]1([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[O:9][CH:8]([CH2:10][O:24][CH3:23])[CH2:7][O:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 10942334Sodium MethoxideHCID 20026689HCID 20026689, compound

Product 1

HCID 20026687HCID 20026687, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6.0 g of 3-[2-(2,4-dichlorobenzyl)-4-chloromethyl-1,3-dioxolan-2-yl] pyridine, 1.8 g of sodium methylate and a catalytically acting amount of sodium iodide are stirred in 50 ml of dimethyl sulfoxide for 20 h at an internal temperature of +120° C. After cooling to RT, the reaction mixture is poured into 400 ml of water, and extracted twice with 120 ml of ethyl acetate each time. The organic phases are combined, washed with 150 ml of water, dried over sodium sulfate, treated with active charcoal and filtered, and the solvent is evaporated off. The oily residue is purified by chromatography on silica gel with ether. The compound is obtained as colourless oil; nD22.5 :1.4774.

Workup

  1. extractionextracted twice with 120 ml of ethyl acetate each time
  2. washwashed with 150 ml of water
  3. dry with materialdried over sodium sulfate
  4. additiontreated with active charcoal
  5. filtrationfiltered
  6. customthe solvent is evaporated off
  7. customThe oily residue is purified by chromatography on silica gel with ether
  8. customThe compound is obtained as colourless oil

Sources & evidence

ORD record
ord-f4bfe38bc89e4e8996bc36ac8538d2db
Source dataset
uspto-grants-1989_08
Patent number
US04859687

Reaction notes

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