Water → HCID 13532505, compound

HRID 1249396Notes

Reaction equation

HRID 1249396 reaction equation
Br[CH:2](C)[C:3](=[O:15])[CH:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH3:5].[C:17](=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[N:29]=[C:28]([OH:30])[CH:27]=[CH:26][CH:25]=1.O>CC(C)=O>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][O:6][C:4]([CH3:5])([CH3:17])[C:3](=[O:15])[CH2:2][O:30][C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:23])[N:29]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 20224643HCID 20224643, compoundHCID 1785160256-chloropyridin-2-ol

Product 1

HCID 13532505HCID 13532505, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

31 g (0.1 mol) of 1-bromo-3-(4-chlorobenzyloxy)-methyl-2-butanone in 200 ml of acetone are heated under reflux with 14 g (0.1 mol) of potassium carbonate and 13 g (0.1 mol) of 6-chloro-2-hydroxypyridine for 6 hours. Thereafter, the reaction mixture is poured into water and extracted with methylene chloride. The organic phase is dried over sodium sulphate and concentrated. 31.5 g (89% of theory) of 3-(4-chlorobenzyloxy)-1-(6-chloropyridin-2-yloxy)-3-methyl-2-butanone are obtained as a light-coloured oil. ##STR14##

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-92cd8b9c5c4f45beae1e6b48ba08c942
Source dataset
uspto-grants-1986_12
Patent number
US04631288

Reaction notes

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