Potassium Permanganate → (R)-2,2,2-trifluoro-N-(4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

HRID 605850Notes

Reaction equation

HRID 605850 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)=[O:4].[O-:18][Mn](=O)(=O)=O.[K+]>CC(C)=O.O>[F:1][C:2]([F:16])([F:17])[C:3]([NH:5][C@H:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:18])[CH2:8][CH2:7]1)=[O:4]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 14511488(R)-2,2,2-trifluoro-N-(1,2,3,4-tetrahydronaphthalen-1-yl)acetamide

Product 1

HCID 59704927(R)-2,2,2-trifluoro-N-(4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl)acetamideYield 91%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a cooled solution of 1 g (4.1 mmol) of (R)-2,2,2-trifluoro-N-(1,2,3,4-tetrahydronaphthalen-1-yl)acetamide in acetone (30 mL) at 0° C., was added a solution of 2.03 g (8.2 mmol) MgSO4.7H2O in 15 mL of water. After 5 min of stirring, 1.95 g (12.3 mmol) of KMnO4 was added in small portions over 1 hr. The mixture was then stirred overnight, slowly warming to room temp. The mixture was filtered. The filtrate was treated with saturated sodium metabisulfite and filtered. The filtrate was extracted with DCM several times. The combined organic extracts were washed with distilled water and brine, dried over MgSO4 and concentrated in vacuo to afford 0.96 g (91%) of the title compound, whose purity was good enough to use crude.

Workup

  1. stirringThe mixture was then stirred overnight
  2. filtrationThe mixture was filtered
  3. additionThe filtrate was treated with saturated sodium metabisulfite
  4. filtrationfiltered
  5. extractionThe filtrate was extracted with DCM several times
  6. washThe combined organic extracts were washed with distilled water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5757f99915ee47c0bff01fcc42f0dc08
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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