Potassium Carbonate → HCID 20193577, compound

HRID 364785Notes

Reaction equation

HRID 364785 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:16]([Cl:17])=[C:15]2[C:11]([CH2:12][C:13]([CH2:20][CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)([CH3:19])[C:14]2=[O:18])=[CH:10][C:9]=1[OH:26].[F:27][C:28]([F:34])([F:33])[S:29](Cl)(=[O:31])=[O:30]>CN(C)C=O>[F:27][C:28]([F:34])([F:33])[S:29]([O:26][C:9]1[CH:10]=[C:11]2[C:15](=[C:16]([Cl:17])[C:8]=1[Cl:7])[C:14](=[O:18])[C:13]([CH2:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25]1)([CH3:19])[CH2:12]2)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79000Trifluoromethanesulfonyl chlorideHCID 13646816HCID 13646816, compound

Product 1

HCID 20193577HCID 20193577, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Anhydrous potassium carbonate (17.7 g., 0.128 mole) is added to a solution of 6,7-dichloro-2-cyclopentylmethyl-2,3-dihydro-5-hydroxy-2-methyl-1H-inden-1-one (13.35 g., 0.0426 mole) in dry dimethylformamide (60 ml.). The suspension is stirred for 1 hour at room temperature, cooled to 15° C. and then trifluoromethanesulfonyl chloride is added at 15°-18° C. After stirring for 1 hour at room temperature, the reaction mixture is poured into ice water (700 ml.). The oil that separates is extracted with ether (125 ml.). The combined organic extracts are washed with water, dried over magnesium sulfate and concentrated in vacuo to obtain the amber, oily product (18.8 g.), which is used in the next step without further purification.

Workup

  1. temperaturecooled to 15° C.
  2. stirringAfter stirring for 1 hour at room temperature
  3. extractionThe oil that separates is extracted with ether (125 ml.)
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain the amber, oily product (18.8 g.), which
  8. customis used in the next step without further purification

Sources & evidence

ORD record
ord-8f7ef1f996cb4162a2bedb370ccc099b
Source dataset
uspto-grants-1986_08
Patent number
US04605664

Reaction notes

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