Methyl 3-formylbenzoate → Methyl 3-[2(E)-(quinolin-2-yl)ethenyl]benzoate

HRID 54527노트

반응식

HRID 54527 반응식
C([Li])CCC.[Cl-].[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH2:17][PH3+].[CH:19]([C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25])=O>CCCCCC.O1CCCC1.O>[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1/[CH:17]=[CH:19]/[C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][CH:30]=1)[C:24]([O:26][CH3:27])=[O:25]

참가 물질

7

반응물 3

HCID 639145Methyl 3-formylbenzoateHCID 19959097Quinolin-2-ylmethylphosphonium chlorideHCID 178418339Butyllithium

생성물 1

HCID 19959111Methyl 3-[2(E)-(quinolin-2-yl)ethenyl]benzoate

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-75 °C

실험 절차

2.5M Butyl lithium in hexane (8.8 ml) is added over 5 minutes to a stirred solution of quinolin-2-ylmethylphosphonium chloride (9.66 g, 22 mmol) in dry tetrahydrofuran (250 ml) at -75° C. The mixture is stirred for 1 hour at -75° C. then a solution of methyl 3-formylbenzoate (3.28 g, 20 mmol) in tetrahydrofuran (25 ml) is added dropwise over 10 minutes. After stirring for a further 30 minutes at -75° C., the mixture is warmed to room temperature, diluted with water and extracted with ethyl acetate. The extract is dried and evaporated and the residue is purified by chromatography on silica eluting with ethyl acetate-hexane (1:3).

후처리

  1. stirringAfter stirring for a further 30 minutes at -75° C.
  2. temperaturethe mixture is warmed to room temperature
  3. extractionextracted with ethyl acetate
  4. customThe extract is dried
  5. customevaporated
  6. customthe residue is purified by chromatography on silica eluting with ethyl acetate-hexane (1:3)

출처 및 근거

ORD 기록
ord-4e243abca980471d981fb852570dde9a
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622969

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