Water → HCID 13646819, compound

HRID 364346Notes

Reaction equation

HRID 364346 reaction equation
[CH:1]1([C:6]2([CH3:19])[CH2:14][C:13]3[C:8](=[C:9]([Cl:17])[C:10]([Cl:16])=[C:11]([OH:15])[CH:12]=3)[C:7]2=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH:29]=[CH2:30].O>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:15][CH2:30][CH2:29][CH:28]=[CH2:27]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 21241Homoallyl bromideHCID 123955886,7-Dichloro-2-cyclopentyl-5-hydroxy-2-methylindan-1-one

Product 1

HCID 13646819HCID 13646819, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Cyclopentyl-6,7-dichloro-2,3-dihydro-2-methyl-5-hydroxy-1H-inden-1-one (12 gm., 0.04 mole) is dissolved in dimethylformamide (30 m.) and treated with potassium carbonate (5.5 gm., 0.04 mole). The mixture is stirred and heated on a steam bath for 30 minutes and 4-bromo-1-butene (5.5 gm., 0.04 mole) is added and the mixture stirred and heated at 60° C. for 24 hours. The reaction mixture is poured into water (300 ml.) and, after standing, the product removed by filtration, dried and recrystallized from petroleum ether. The yield is 11.5 gm., m.p. 63°-65° C.

Workup

  1. temperatureheated on a steam bath for 30 minutes
  2. stirringthe mixture stirred
  3. customthe product removed by filtration
  4. customdried
  5. customrecrystallized from petroleum ether

Sources & evidence

ORD record
ord-adaac7031f5f48a1b6330741c95f6d38
Source dataset
uspto-grants-1986_08
Patent number
US04604403

Reaction notes

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