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

HRID 2257058노트

반응식

HRID 2257058 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7a43eae2cfaa47ac8de99cf0fa63df2d
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05656639

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