Dimethyl Sulfoxide → HCID 13532506, compound

HRID 1249395Notes

Reaction equation

HRID 1249395 reaction equation
[H-].[Na+].[I-].C[S+](C)(C)=O.[CH3:9]S(C)=O.[Cl:13][C:14]1[CH:35]=[CH:34][C:17]([CH2:18][O:19][C:20]([CH3:33])([CH3:32])[C:21](=[O:31])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[N:25]=2)=[CH:16][CH:15]=1>O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][O:19][C:20]([C:21]2([CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[N:25]=3)[CH2:9][O:31]2)([CH3:32])[CH3:33])=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 13532505HCID 13532505, compound

Product 1

HCID 13532506HCID 13532506, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

1.5 g (0.05 mol) of 80% pure sodium hydride are added in portions to a mixture of 11 g (0.05 mol) of trimethylsulphoxonium iodide and 60 ml of dimethylsulphoxide at 10° C., with stirring. The reaction mixture is stirred for 15 minutes, 17.7 g (0.05 mol) of 3-(4-chlorobenzyloxy)-(6-chloropyridin-2-yloxy)-3-methyl-2-butanone in a little dimethylsulphoxide are then added dropwise and the mixture is warmed at 60° C. for 1 hour. It is subsequently poured into water, under a nitrogen atmosphere, and extracted with methylene chloride. The organic phase is dried over sodium sulphate and concentrated. The crude 2-[2-(4-chlorobenzyloxy)-prop-2-yl]-2-(6-chloropyridin-2-yloxymethyl)-oxirane thus obtained is further reacted directly. ##STR13##

Workup

  1. stirringThe reaction mixture is stirred for 15 minutes
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f409a5f2a1cc4bafb2c88f5da30c4ee0
Source dataset
uspto-grants-1986_12
Patent number
US04631288

Reaction notes

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