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

HRID 1363225Notes

Reaction equation

HRID 1363225 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 solution of (R)-2,2,2-trifluoro-N-(1,2,3,4-tetrahydronaphthalen-1-yl)acetamide (1 g) in acetone (30 mL) at 0° C. was added a solution of MgSO4.7H2O (2.0 g) in water (15 mL). After 5 min of stirring, KMnO4 (2 g) was added in small portions over 1 hr. The mixture was then stirred overnight, slowly warming to room temp. Celite was added and 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. 1H-NMR (300 MHz, CDCl3) □ 8.2 (d, 1H), 7.7 (t, 1H), 7.6 (t, 1H), 7.5 (d, 1H), 6.8 (broad s, 1H), 5.5 (m, 1H), 2.9 (m, 2H), 2.6 (m 1H), 2.4 (m, 1H) ppm.

Workup

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

Sources & evidence

ORD record
ord-1b165cc1054440ce898995f7fa79f698
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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