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

HRID 1198522ノート

反応式

HRID 1198522 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-75 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bc50303f2be34977a7bdbc289cdd72a0
出典データセット
uspto-grants-1994_01
特許番号
US05281593

反応ノート

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