Nitrogen → 2-Butyl-6,7-dichloro-2-cyclopentyl-5-methoxy-1-indanone

HRID 1463135Notes

Reaction equation

HRID 1463135 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].N#N.CC(C)([O-])C.[K+].[CH2:28](I)[CH2:29][CH2:30][CH3:31]>C1C=CC=CC=1.C(O)(C)(C)C.O>[CH2:28]([C:7]1([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:6][C:5]2[C:9](=[C:10]([Cl:11])[C:2]([Cl:1])=[C:3]([O:18][CH3:19])[CH:4]=2)[C:8]1=[O:12])[CH2:29][CH2:30][CH3:31]

Participants

8

Reactant 4

HCID 947NitrogenHCID 10962Butyl iodideHCID 123955576,7-Dichloro-2-cyclopentyl-5-methoxy-2,3-dihydroinden-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 127611342-Butyl-6,7-dichloro-2-cyclopentyl-5-methoxy-1-indanone

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 6,7-dichloro-2-cyclopentyl-2,3-dihydro-5-methoxy-1H-inden-1-one (7.2 g) in benzene (70 ml) was heated at reflux in a N2 atmosphere and treated over a 5 minute period with a solution of potassium t-butoxide (4.2 g) in t-butanol (70 ml). The solution was refluxed for 3/4 hour, treated with butyl iodide (11 ml), refluxed for an additional 3/4 hour, cooled, treated with water (50 ml) and the organic solvents were distilled at reduced pressure. The aqueous slurry was extracted with ether washed with water, dried over MgSO4 and evaporated at reduced pressure. Treatment of the residue with hexane (100 ml) gave 6.9 g of 2-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-5-methoxy-1H-inden-1-one, m.p. 122°-123° C.

Workup

  1. temperatureThe solution was refluxed for 3/4 hour
  2. temperaturerefluxed for an additional 3/4 hour
  3. temperaturecooled
  4. distillationthe organic solvents were distilled at reduced pressure
  5. extractionThe aqueous slurry was extracted with ether
  6. washwashed with water
  7. dry with materialdried over MgSO4
  8. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-594d3a0c5cdb42a6b01db91509bbb6e5
Source dataset
uspto-grants-1984_07
Patent number
US04463208

Reaction notes

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