Water → HCID 14302201, compound

HRID 867519Notes

Reaction equation

HRID 867519 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].Br[CH2:21][CH2:22][CH2:23][C:24]#[N:25].C(=O)([O-])[O-].[K+].[K+].O>CN(C)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][CH2:21][CH2:22][CH2:23][C:24]#[N:25])[CH:4]=3)[C:8]2=[O:12])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 123955886,7-Dichloro-2-cyclopentyl-5-hydroxy-2-methylindan-1-one

Product 1

HCID 14302201HCID 14302201, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6,7-dichloro-2-cyclopentyl-5-hydroxy-2-methyl-2,3-dihydro-1H-inden-1-one (6.0 g, 20 mmole), 4-bromobutanenitrile (3.28 g, 22 mmole), and potassium carbonate (3.1 g, 22 mmole) in dimethylformamide (50 ml) was stirred at 60°-65° for four hours. The reaction mixture was poured into water and extracted with diethyl ether. The organic layer was washed successively with water and brine, dried over magnesium sulfate, and concentrated in vacuo to a solid residue (4.7 g). Recrystallization from butyl chloride-hexane afforded the analytically pure title compound, m.p. ca. 112°.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed successively with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo to a solid residue (4.7 g)
  5. customRecrystallization from butyl chloride-hexane

Sources & evidence

ORD record
ord-ea67b0d65aa341e6b253201db14594e6
Source dataset
uspto-grants-1988_10
Patent number
US04775695

Reaction notes

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