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

HRID 605850ノート

反応式

HRID 605850 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5757f99915ee47c0bff01fcc42f0dc08
出典データセット
uspto-grants-2011_03
特許番号
US07915268B2

反応ノート

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