Butyl iodide → HCID 67361498, compound

HRID 1984795Notes

Reaction equation

HRID 1984795 reaction equation
[H-].[Na+].[CH:3]1([CH:8]([C:14]([CH3:16])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1.[H][H].I[CH2:20][CH2:21][CH2:22][CH3:23]>CN(C)C=O>[CH2:20]([C:8]([CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7]1)([C:14]([CH3:16])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 17750296Ethyl 2-cyclopentyl-3-oxobutanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 67361498HCID 67361498, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A mechanically stirred suspension of sodium hydride (4.00 g of 60% dispersion in mineral oil) in anhydrous N,N-dimethylformamide (DMF, 100 mL) was treated dropwise with a solution of ethyl 2-cyclopentyl-3-methyl-3-oxo-propionate (17.7 g) in DMF (50.0 mL) at room temperature under nitrogen atmosphere. Stirring of the reaction mixture was continued at this temperature until the formation of hydrogen ended and the reaction mixture became transparent. After that the mixture was treated dropwise with a solution of 1-iodobutane (19.9 g) in DMF (50 mL) and stirred at room temperature overnight. The reaction mixture was then quenched by pouring onto a mixture of ice and 10% aqueous hydrochloric acid. The formed organic phase was separated and the aqueous phase was extracted with hexane. The combined organic phases were washed with brine, dried over magnesium sulfate, filtered, concentrated on a rotary evaporator, and distilled in vacuum to give 16.1 g (70%) of the title compound.

Workup

  1. stirringstirred at room temperature overnight
  2. customThe reaction mixture was then quenched
  3. additionby pouring onto a mixture of ice and 10% aqueous hydrochloric acid
  4. customThe formed organic phase was separated
  5. extractionthe aqueous phase was extracted with hexane
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated on a rotary evaporator
  10. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-cb994275229648239f35ffd012269684
Source dataset
uspto-grants-2009_06
Patent number
US07544748B2

Reaction notes

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