Sodium hydride → HCID 10243028, compound

HRID 1494084Notes

Reaction equation

HRID 1494084 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][C:10]#[N:11])[CH:4]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18]>CN(C)C=O>[C:10]([CH:9]([C:5]1[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=1)[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])#[N:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79557Methyl 5-bromovalerateHCID 809233-Pyridineacetonitrile

Product 1

HCID 10243028HCID 10243028, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 8.6 g of sodium hydride (50% dispersion in mineral oil) in 200 mL of dimethylformamide is added in a solution of 17.7 g of 3-pyridylacetonitrile in 15 mL of dimethylformamide over a period of 0.5 hour. The reaction is stirred for a further 0.5 hour at room temperature, then cooled to -20° before adding 30 g of methyl 5-bromovalerate. The reaction is then allowed to warm up to room temperature over a period of several hours and left to stand for 18 hours. The reaction is then poured into 300 mL of ice water and extracted with 300 mL of ethyl acetate. The extract is washed with 3 portions of 75 mL of 1N hydrochloric acid and the aqueous solution neutralized with ammonium hydroxide and extracted with ethyl acetate. The extract is dried over magnesium sulfate, filtered and evaporated to yield methyl 6-cyano-6-(3-pyridyl)-hexanoate.

Workup

  1. temperaturecooled to -20°
  2. temperatureto warm up to room temperature over a period of several hours
  3. waitleft
  4. waitto stand for 18 hours
  5. extractionextracted with 300 mL of ethyl acetate
  6. washThe extract is washed with 3 portions of 75 mL of 1N hydrochloric acid
  7. extractionextracted with ethyl acetate
  8. dry with materialThe extract is dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-3abd6d86b0be43eca8344dc9634f9298
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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