Potassium Permanganate → HCID 117831487, compound

HRID 525312Notes

Reaction equation

HRID 525312 reaction equation
[CH2:1]([C:37]([O:39]CC)=[O:38])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22].CC([O-])(C)C.[K+].[O-][Mn](=O)(=O)=O.[K+]>CC(O)(C)C>[C:33]([O:32][C:30]([C:11]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][C:37]([OH:39])=[O:38])=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

5

Reactant 3

HCID 516875Potassium PermanganateHCID 23665647Potassium tert-butoxideHCID 117831276HCID 117831276, compound

Product 1

HCID 117831487HCID 117831487, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a solution of compound from step 3 (0.037 mmol) in tBuOH (1 mL) is added a solution of KOtBu (114 mg, 1.012 mmol) in tBuOH (2 mL) at 30° C. under N2. The mixture is stirred at r.t. and monitored by TLC (1:1 EtOAc/hexanes, KMnO4, reflux). After the reaction is completed, the reaction mixture is quenched with 1 M HCl (20 mL) and extracted twice with EtOAc (25 mL). The organic layers are combined, dried over Na2SO4, filtered and concentrated. The material was carried on to the next step without further purification.

Workup

  1. customthe reaction mixture is quenched with 1 M HCl (20 mL)
  2. extractionextracted twice with EtOAc (25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe material was carried on to the next step without further purification

Sources & evidence

ORD record
ord-6c2d16dd7bbd4a6a9cc511791a12a8c8
Source dataset
uspto-grants-2016_05
Patent number
US09340582B2

Reaction notes

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