Methyl iodide → 2-Cyclopentyl-2-methyl-5-methoxy-6,7-dichloro-1-indanone

HRID 358271Notes

Reaction equation

HRID 358271 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][CH:7]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:8]2=[O:12])=[CH:4][C:3]=1[O:18][CH3:19].[H-].[Na+].[H][H].CI.Cl[C:27]1(OC)C(Cl)=CC2C(=O)C(C3CCCC3)(C)CC=2C1>COCCOC>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)([CH3:27])[C:8]2=[O:12])=[CH:4][C:3]=1[O:18][CH3:19]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 123955576,7-Dichloro-2-cyclopentyl-5-methoxy-2,3-dihydroinden-1-oneHCID 705020795,6-dichloro-2-cyclopentyl-2,3-dihydro-5-methoxy-2-methyl-1H-inden-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 123955682-Cyclopentyl-2-methyl-5-methoxy-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

6,7-Dichloro-2-cyclopentyl-2,3-dihydro-5-methoxy-1H-inden-1-one (7.5 g., 0.025 mole) is dissolved in dry 1,2-dimethoxyethane (200 ml.) under nitrogen. Sodium hydride (57% in mineral oil; 1.16 g., 0.0275 mole) is then added and the mixture is stirred at 80° until evolution of hydrogen ceases (2 hours). The solution is cooled and methyl iodide (7.5 ml.) is added, the mixture is again brought to reflux and then cooled. Most of the 1,2-dimethoxyethane is evaporated and water is added to the residue which soon solidifies and is crystallized from methylcyclohexane and from ethanol-water (4:1) to obtain 3.4 g. of 5,6-dichloro-2-cyclopentyl-2,3-dihydro-5-methoxy-2-methyl-1H-inden-1-one, m.p. 109°-111.5° C.

Workup

  1. temperatureThe solution is cooled
  2. temperatureto reflux
  3. temperaturecooled
  4. customMost of the 1,2-dimethoxyethane is evaporated
  5. additionwater is added to the residue which
  6. customis crystallized from methylcyclohexane and from ethanol-water (4:1)
  7. customto obtain 3.4 g

Sources & evidence

ORD record
ord-39bd836e6ac84631ae0771142345ec32
Source dataset
uspto-grants-1984_08
Patent number
US04465850

Reaction notes

Loading…