Potassium Carbonate → HCID 13646821, compound

HRID 364348Notes

Reaction equation

HRID 364348 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-f7ab345fd42d49b58e25fb610187e4f2
Source dataset
uspto-grants-1986_08
Patent number
US04604403

Reaction notes

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