Potassium Permanganate → HCID 66802165, compound

HRID 1057209Notes

Reaction equation

HRID 1057209 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[C:7]1(/[C:13](/[CH2:42][CH3:43])=[C:14](\[C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[CH:36]=[C:35]([CH:40]=[O:41])[CH:34]=[CH:33]3)/[C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[N:19]=[CH:18]3)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CC(C)=O.O>[C:7]1(/[C:13](/[CH2:42][CH3:43])=[C:14](\[C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[CH:36]=[C:35]([C:40]([OH:2])=[O:41])[CH:34]=[CH:33]3)/[C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[N:19]=[CH:18]3)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 86695292HCID 86695292, compound

Product 1

HCID 66802165HCID 66802165, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Potassium permanganate (5 mL of 1.0 M aqueous solution) was added to a solution of (E)-6-(2-phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)-2-naphthaldehyde (240 mg, 0.49 mmol) and acetone:H2O (2:1, 15 mL) at room temperature. The reaction was stirred for 3 h, quenched with sat. Na2SO3, acidified to pH 5 with 1.0 M aqueous HCl soln, and then extracted with 2× EtOAc. The organic layers were combined, washed with water then brine, dried over Na2SO4, and concentrated. The crude material was used without further purification. LCMS: 419 [(M-THP+H)+H]+.

Workup

  1. customquenched with sat. Na2SO3
  2. extractionextracted with 2× EtOAc
  3. washwashed with water
  4. dry with materialbrine, dried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude material was used without further purification

Sources & evidence

ORD record
ord-69577e499b144c699d6f9b5d60493197
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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