Potassium Carbonate → HCID 13646821, compound

HRID 1982720Notes

Reaction equation

HRID 1982720 reaction equation
[CH:1]1([C:6]2([CH3:19])[CH:14](O)[C:13]3[C:8](=[C:9]([Cl:17])[C:10]([Cl:16])=[CH:11][CH:12]=3)[C:7]2=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-:21].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32]>CN(C)C=O>[Cl:16][C:10]1[C:9]([Cl:17])=[C:8]2[C:13]([CH2:14][C:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)([CH3:19])[C:7]2=[O:18])=[CH:12][C:11]=1[O:21][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79557Methyl 5-bromovalerateHCID 20193579HCID 20193579, compound

Product 1

HCID 13646821HCID 13646821, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Cyclopentyl-6,7-dichloro-2,3-dihydro-2-methyl-hydroxy-1H-inden-1-one (12 g., 0.04 mole) is dissolved in dimethylformamide (30 ml) and treated with potassium carbonate (5.5 g., 0.04 mole). Methyl 5-bromopentanoate (8.5 g., 0.04 mole) is added dropwise with good stirring over a period of 30 minutes. Then, the mixture is stirred and heated in a steam bath for two hours. The mixture is cooled and poured in to ice water (300 ml.). The product which solidifies upon standing is removed by filtration. The yield is 15.1 g., m.p. 83°-86° C. Upon recrystallization from petroleum ether the methyl 5-[(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)oxy]pentanoate melts at 85°-88° C.

Workup

  1. stirringThen, the mixture is stirred
  2. temperatureheated in a steam bath for two hours
  3. temperatureThe mixture is cooled
  4. customupon standing is removed by filtration
  5. customUpon recrystallization from petroleum ether the methyl 5-[(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)oxy]pentanoate melts at 85°-88° C.

Sources & evidence

ORD record
ord-f2f5397dfbf54a0a936d218e1afefa3d
Source dataset
uspto-grants-1986_06
Patent number
US04596821

Reaction notes

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