Sodium hydride → Ethyl 5-cyano-5-(3,4-dichlorophenyl)pentanoate

HRID 342679Notes

Reaction equation

HRID 342679 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]#[N:13])[CH:7]=[CH:8][C:9]=1[Cl:10].Br[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1>[C:12]([CH:11]([C:6]1[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=1)[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])#[N:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 76690(3,4-Dichlorophenyl)acetonitrile

Product 1

HCID 22741808Ethyl 5-cyano-5-(3,4-dichlorophenyl)pentanoateYield 42.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

5.9 g of sodium hydride as a 55% dispersion in oil are suspended in 50 ml of THF; the suspension is cooled in an ice bath and 25 g of 3,4-dichlorophenylacetonitrile in 25 ml of THF are added dropwise; the mixture is cooled again in an ice bath and a solution of 26.21 g of ethyl 4-bromobutanoate in 25 ml of THF is added dropwise. After one night at RT, the mixture is evaporated to dryness and the residue is then taken up with 2N hydrochloric acid solution and extracted with ether. The extract is washed with 2N hydrochloric acid solution and then with saturated sodium chloride solution. The organic phase is dried over MgSO4 and then concentrated under vacuum and the residue is chromatographed on silica using pure toluene up to a toluene/AcOEt mixture (100/3; v/v) as the eluent to give 17 g of the expected product.

Workup

  1. temperaturethe suspension is cooled in an ice bath
  2. temperaturethe mixture is cooled again in an ice bath
  3. waitAfter one night at RT
  4. customthe mixture is evaporated to dryness
  5. extractionextracted with ether
  6. washThe extract is washed with 2N hydrochloric acid solution
  7. dry with materialThe organic phase is dried over MgSO4
  8. concentrationconcentrated under vacuum
  9. customthe residue is chromatographed on silica using pure toluene up to a toluene/AcOEt mixture (100/3; v/v) as the eluent

Sources & evidence

ORD record
ord-8879f60fec1044e3bd112e09c0af306f
Source dataset
uspto-grants-1999_01
Patent number
US05859029

Reaction notes

Loading…