Potassium Hydroxide → AG-H-13688

HRID 1462861Notes

Reaction equation

HRID 1462861 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:18])([CH2:16]O)[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.CS(Cl)(=O)=O.[OH-].[K+]>N1C=CC=CC=1.CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH2:16][O:18]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 31297Methanesulfonyl chlorideHCID 133368182-(2,4-Dichlorophenyl)-3-(1H-imidazol-1-yl)propane-1,2-diol

Product 1

HCID 2783908AG-H-13688Yield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

To an ice-cooled solution of (-)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2,3-propanediol (5.4 g) in pyridine (50 ml) was added dropwise methanesulfonyl chloride (2.15 g). The reaction mixture was stirred at 0°-10° C. for 2 hours. An ice-cooled solution of 85.5% potassium hydroxide (3.7 g) in methanol (60 ml) was added dropwise thereto, and then the mixture was stirred at 0°-10° C. for 1 hour. The solvent was removed in vacuo, and the residue was extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and evaporated to give a red oil. The oily residue was purified by chromatography on silica gel (60 g) with chloroform as a solvent and recrystallized from ether-hexane to give (-)-2-(2,4-dichlorophenyl)-2-(imidazol-1-yl)methyloxirane (4.3 g) as colorless needles. Yield, 84.6%. M.P., 107°-108.5° C. [α]D21.5, -8.4° (C=1.0, MeOH).

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred at 0°-10° C. for 1 hour
  3. customThe solvent was removed in vacuo
  4. extractionthe residue was extracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto give a red oil
  9. customThe oily residue was purified by chromatography on silica gel (60 g) with chloroform as a solvent
  10. customrecrystallized from ether-hexane

Sources & evidence

ORD record
ord-1aa284a4cbe24870b5f56b3c29bcefc9
Source dataset
uspto-grants-1984_07
Patent number
US04461774

Reaction notes

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