Potassium Carbonate → 2-Cyclopentyl-6,7-dichloro-2-methyl-5-trifluoromethylsulfonyloxy-1-indanone

HRID 1413234Notes

Reaction equation

HRID 1413234 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[OH:19].C(=O)([O-])[O-].[K+].[K+].[F:26][C:27]([F:33])([F:32])[S:28](Cl)(=[O:30])=[O:29]>CC(C)=O>[CH:14]1([C:7]2([CH3:13])[CH2:6][C:5]3[C:9](=[C:10]([Cl:11])[C:2]([Cl:1])=[C:3]([O:19][S:28]([C:27]([F:33])([F:32])[F:26])(=[O:30])=[O:29])[CH:4]=3)[C:8]2=[O:12])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79000Trifluoromethanesulfonyl chlorideHCID 123955886,7-Dichloro-2-cyclopentyl-5-hydroxy-2-methylindan-1-one

Product 1

HCID 125402562-Cyclopentyl-6,7-dichloro-2-methyl-5-trifluoromethylsulfonyloxy-1-indanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6,7-dichloro-2-cyclopentyl-5-hydroxy-2-methyl-1-indanone (20.93 g., 0.07 mole), anhydrous potassium carbonate (25.99 g., 0.188 mole) and dry acetone (350 ml) are stirred at room temperature and treated with trifluoromethane sulfonyl chloride (12.70 g., 0.0754 mmole) in portions. Reaction is complete in about 15 minutes after the completion of the addition. The mixture is filtered and evaporated to dryness. The residue is dissolved in methylene chloride, the solution dried (MgSO4) and evaporated under vacuum to an oil giving 28.45 g. (94%),

Workup

  1. customReaction
  2. additionafter the completion of the addition
  3. filtrationThe mixture is filtered
  4. customevaporated to dryness
  5. dissolutionThe residue is dissolved in methylene chloride
  6. dry with materialthe solution dried (MgSO4)
  7. customevaporated under vacuum to an oil
  8. customgiving 28.45 g

Sources & evidence

ORD record
ord-2ccae35062f5413eba9527c665b3537e
Source dataset
uspto-grants-1981_02
Patent number
US04249021

Reaction notes

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