Hydrochloric Acid → 1-Phenylcyclopentanecarbonitrile

HRID 1409551

반응식

HRID 1409551 반응식
[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16]Br.Cl>CS(C)=O.O.CCOCC>[C:3]1([C:9]2([C:10]#[N:11])[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 80561,4-DibromobutaneHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

생성물 1

HCID 661681-Phenylcyclopentanecarbonitrile수율 86.7%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

To a suspension of NaH (11.3 g, 281.7 mmol, 60%) in DMSO (75 ml) were added dropwise a mixture of phenyl-acetonitrile (15 g, 128.0 mmol) and 1,4-dibromo-butane (18 ml, 128.0 mmol) dissolved in DMSO:Ether (150 ml, 1:1) at 0° C. and the reaction mixture was stirred at room temperature (RT) for 2 to 3 h. After completion of the reaction, water and 10% HCl solution were added to the crude mass. It was extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated and purified by column chromatography (10% EtOAc-hexane) to get 1-phenyl-cyclopentanecarbonitrile (2) (19 g, 86.64%) as a yellow solid. MS: m/z=171 (MH+).

후처리

  1. additionwere added dropwise
  2. additionwere added to the crude mass
  3. extractionIt was extracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography (10% EtOAc-hexane)

출처 및 근거

ORD 기록
ord-b4203385e32e47fda13e193367799b70
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921388B2

연결된 노트

불러오는 중…