Water → HCID 15096597, compound

HRID 345454Notes

Reaction equation

HRID 345454 reaction equation
[OH-].[Na+].N1C=[CH:6][N:5]=[N:4]1.[C:8]([C:12]1([C@@H:15]2[CH2:17][C@H:16]2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[CH2:14][O:13]1)([CH3:11])([CH3:10])[CH3:9].O.[CH3:27][N:28]1CCCC1=O>>[C:8]([C:12]([C@@H:15]1[CH2:17][C@H:16]1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])([OH:13])[CH2:14][N:5]1[CH:6]=[N:28][CH:27]=[N:4]1)([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 5

HCID 962WaterHCID 13387N-methyl-2-pyrrolidone2×HCID 14798Sodium HydroxideHCID 15096596HCID 15096596, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 15096597HCID 15096597, compoundYield 60%

Conditions

Temperature
50 °C

Procedure

5.6 g of sodium hydroxide (50% by weight) are added to a solution of 5.1 g of triazole in 50 ml of N-methylpyrrolidone, and the mixture is heated at 50° C. for 30 minutes. Then, at room temperature, 10 g of trans-1-(2-tert-butyl-2-oxiranyl)-2-(2,4-dichlorophenyl)cyclopropane which is dissolved in 50 ml of N-methylpyrrolidone are slowly added dropwise. The reaction mixture is stirred at room temperature for 18 hours and then 100 ml of water are added to the solution and the mixture is extracted several times with methyl tert-butyl ether. The isolated organic phase is washed twice with water and then dried over sodium sulfate and concentrated. The remaining residue is purified by flash chromatography on silica gel (9:1 ethyl acetate/n-hexane), resulting in separation of the diastereomers. 7.4 g (60% overall yield) of trans-1-[1-tert-butyl-1-hydroxy-2-(1,2,4-triazol-1-yl)ethyl]-2-(2,4-dichlorophenyl)cyclopropane are obtained.

Workup

  1. additionare slowly added dropwise
  2. extractionthe mixture is extracted several times with methyl tert-butyl ether
  3. washThe isolated organic phase is washed twice with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe remaining residue is purified by flash chromatography on silica gel (9:1 ethyl acetate/n-hexane)
  7. customresulting in separation of the diastereomers

Sources & evidence

ORD record
ord-cbd99e80757c41b09382fb68c6e81bb8
Source dataset
uspto-grants-1991_10
Patent number
US05057532

Reaction notes

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