Potassium Hydroxide → HCID 86670009, compound

HRID 920530Notes

Reaction equation

HRID 920530 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:6]=1[C:16]([F:19])([F:18])[F:17])=[O:4].[BH4-].[Na+].[OH-].[K+]>O1CCOCC1.O>[O:4]1[CH2:2][CH:3]1[C:5]1[CH:10]=[CH:9][C:8]([O:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:6]=1[C:16]([F:19])([F:18])[F:17]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 4311764Sodium borohydrideHCID 86670010HCID 86670010, compound

Product 1

HCID 86670009HCID 86670009, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methanesulfonic acid 4-(2-bromo-acetyl)-3-trifluoromethyl-phenyl ester (33.95 g; 89.3 mmol) in 1,4-dioxane (150 mL) was added dropwise a solution of NaBH4 (2.37 g; 62.5 mmol) in water (47 mL). The resulting mixture was stirred at RT for 2.5 hours, subsequently, quenched with 0.5M aqueous HCl (125 mL), and extracted with EtOAc. The combined organic layers were washed with water, dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in Et2O (500 mL) and treated with a solution of KOH (4.19 g; 74.7 mmol) in water (100 mL). The resulting mixture was heated under reflux for 4 hours. After cooling to RT, the volatiles were removed in vacuo and the residue was partitioned between EtOAc and water. The organic layer was washed with water, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (CH2Cl2) to afford methanesulfonic acid 4-oxiranyl-3-trifluoromethyl-phenyl ester (23.54 g).

Workup

  1. customsubsequently, quenched with 0.5M aqueous HCl (125 mL)
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in Et2O (500 mL)
  8. temperatureThe resulting mixture was heated
  9. temperatureunder reflux for 4 hours
  10. temperatureAfter cooling to RT
  11. customthe volatiles were removed in vacuo
  12. customthe residue was partitioned between EtOAc and water
  13. washThe organic layer was washed with water
  14. dry with materialdried (MgSO4)
  15. filtrationfiltered
  16. concentrationconcentrated in vacuo
  17. customThe residue was purified by column chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-2db02ea680bb4c30a03e9bf5b3c5b241
Source dataset
uspto-grants-2016_03
Patent number
US09273017B2

Reaction notes

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