Water → Ethyl (2Z)-2-azido-3-(4-bromophenyl)-2-propenoate

HRID 1169353노트

반응식

HRID 1169353 반응식
[O-]CC.[Na+].[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1.[N:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+:15]=[N-:16].O>C(O)C.C1(C)C=CC=CC=1>[N:14](/[C:17](=[CH:10]\[C:9]1[CH:12]=[CH:13][C:6]([Br:5])=[CH:7][CH:8]=1)/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+:15]=[N-:16]

참가 물질

7

반응물 4

HCID 962WaterHCID 69480Acetic acid, azido-, ethyl esterHCID 707414-BromobenzaldehydeHCID 2723922Sodium ethoxide

생성물 1

HCID 24767341Ethyl (2Z)-2-azido-3-(4-bromophenyl)-2-propenoate수율 39%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 1140Toluene용매2회

실험 절차

Into a solution of sodium ethoxide (a 20% solution in ethanol, 22.2 g) in toluene (100 ml) was added at 0° C. over a period of more than 10 minutes a solution of 4-bromobenzaldehyde (10 g) and ethyl azidoacetate (7.0 g) in toluene (50 ml). After being stirred at room temperature for 2 hours, the reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the residue was subjected to separation and purification using column chromatography (ethyl acetate/hexane 1:19) to obtain ethyl (Z)-2-azido-3-(4-bromophenyl)acrylate (6.24 g) as a yellow oily substance.

후처리

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialwas dried with magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was subjected to separation and purification

출처 및 근거

ORD 기록
ord-b5f4680863cc4c45a60cd640bde76739
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627651B1

반응 노트

불러오는 중…