Methyl trifluoromethyl ketone → HCID 86697007, compound

HRID 1887396Notes

Reaction equation

HRID 1887396 reaction equation
[O:1]1[CH2:5][CH:4]=[CH:3][C@H:2]1[C@@H:6]([CH:19]([F:21])[F:20])[CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.FC(F)(F)C(C)=[O:25].C(=O)([O-])[O-].[Na+].[Na+].OOS([O-])=O.[K+]>C(#N)C.O.C(N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC(O)=O.[Na+].[Na+]>[C@H:3]12[O:25][C@H:4]1[CH2:5][O:1][C@@H:2]2[C@@H:6]([CH:19]([F:20])[F:21])[CH2:7][NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 9871Methyl trifluoromethyl ketoneHCID 10340Sodium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 86697008HCID 86697008, compound

Product 1

HCID 86697007HCID 86697007, compoundYield 123.8%

Reagents, catalysts & solvents 3

HCID 8759EDTA disodium saltCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of alkene (104b) (147 mg, 0.49 mmol) in acetonitrile (3.6 mL) and aqueous Na2.EDTA (0.04 mmol solution, 3.6 mL) at 0° C. was added 1,1,1-trifluoroacetone (0.53 mL, 5.9 mmol). To this solution was added in portions a mixture of sodium carbonate (0.352 g, 4.2 mmol) and OXONE® (0.942 g, 1.53 mmol) over a period of 1 hour. The mixture was stirred for 25 minutes then diluted with water (25 mL) and the product extracted into dichloromethane (3×25 mL). The combined organic layers were washed consecutively with water (150 mL), aqueous sodium hydrogen sulphite solution (5%, 25 mL) and brine (25 mL), then dried (Na2SO4), filtered and reduced in vacuo to leave a colourless oil (0.19 g), used without further purification. HPLC-MS 314.1 [M+H]+, 336.1 [M+Na]+.

Workup

  1. additionTo this solution was added in portions
  2. extractionthe product extracted into dichloromethane (3×25 mL)
  3. washThe combined organic layers were washed consecutively with water (150 mL), aqueous sodium hydrogen sulphite solution (5%, 25 mL) and brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-1be090ef45404ad2a22fe5481b920f54
Source dataset
uspto-grants-2013_08
Patent number
US08501744B2

Reaction notes

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