Ethyl Acrylate → Ethyl 4-Cyano-5-methyl-4-(2-thienyl)hexanoate

HRID 1582770노트

반응식

HRID 1582770 반응식
[CH3:1][CH:2]([CH3:11])[CH:3]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:4]#[N:5].[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14].CC(C)([O-])C.[K+].[Cl-].[NH4+]>O1CCCC1.[Cl-].[Na+].O.C(OCC)(=O)C.CCCCCC>[C:4]([C:3]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)([CH:2]([CH3:11])[CH3:1])[CH2:14][CH2:13][C:12]([O:16][CH2:17][CH3:18])=[O:15])#[N:5]

참가 물질

8

반응물 4

HCID 8821Ethyl AcrylateHCID 25517Ammonium ChlorideHCID 123819863-Methyl-2-(2-thienyl)butanenitrileHCID 23665647Potassium tert-butoxide

생성물 1

HCID 22718311Ethyl 4-Cyano-5-methyl-4-(2-thienyl)hexanoate수율 62.5%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 21226206Ethyl acetate hexane용매HCID 57417360Sodium chloride; water용매

실험 절차

3-Methyl-2-(2-thienyl)butane nitrile 5.56 g 33.6 mmol and ethyl acrylate 4.00 ml 37.0 mmol were dissolved in tetrahydrofuran 100 ml. Potassium t-butoxide, 566 mg 5.04 mmol, was added little by little thereto at room temperature. Generation of heat continued during this step. After stirring for 1 hour, brine 100 ml and aqueous saturated ammonium chloride 150 ml were added thereto successively, and the mixture was extracted with ether 1 L. The organic layer was washed with brine 500 ml and water 500 ml successively, dried over magnesium sulfate anhydride and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound (5.57 g 21.0 mmol, 62.5%) was obtained as a yellow oil.

후처리

  1. temperatureGeneration of heat
  2. extractionsuccessively, and the mixture was extracted with ether 1 L
  3. washThe organic layer was washed with brine 500 ml and water 500 ml successively
  4. dry with materialdried over magnesium sulfate anhydride
  5. customevaporated

출처 및 근거

ORD 기록
ord-159b52f2ae32472d8d838766c1bbfc70
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06737425B1

반응 노트

불러오는 중…