Iodoethane → alpha-Cyclopentyl-p-methoxybutyrophenone

HRID 637375Notes

Reaction equation

HRID 637375 reaction equation
[CH:1]1([CH2:6][C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:19](I)[CH3:20]>COCCOC>[CH:1]1([CH:6]([CH2:19][CH3:20])[C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 13175263HCID 13175263, compound

Product 1

HCID 13175264alpha-Cyclopentyl-p-methoxybutyrophenoneYield 2,888.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

α-Cyclopentyl-p-methoxyacetophenone (13.0 g, 0.06 mol) was added slowly in dry DME (DME=Dimethoxyethane) to the suspension of NaH (8 g, 55-60% dispersion, 0.018 mmol) in dry DME under N2 atmosphere at room temperature. The suspension was stirred over night. Ethyl iodide (27.7 g, 0.18 mmol) was added and stirring continued for another two hours. Ice water was added cautiously and the water layer extracted with toluene. The organic layer was washed with water, dried and evaporated to give 12.7 g (0.0052 mol, 86%) of the product.

Workup

  1. stirringstirring
  2. extractionthe water layer extracted with toluene
  3. washThe organic layer was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-2dd6c55b99864fc88ccca63a8507f669
Source dataset
uspto-grants-1985_12
Patent number
US04556677

Reaction notes

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