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

HRID 1198522노트

반응식

HRID 1198522 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) was 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 was stirred for 1 hour at -75° C. then a solution of methyl 3-formylbenzoate (3.28 g, 20 mmol) in tetrahydrofuran (25 ml) was added dropwise over 10 minutes. After stirring for a further 30 minutes at -75° C. the mixture was warmed to room temperature, diluted with water and extracted with ethyl acetate. The extract was dried and evaporated and the residue was purified by chromatography on silica eluting with ethyl acetate-hexane (1:3).

후처리

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

출처 및 근거

ORD 기록
ord-bc50303f2be34977a7bdbc289cdd72a0
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05281593

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