2-Quinolinecarboxaldehyde → (Z)-2-(2-Bromovinyl)quinoline

HRID 920895

반응식

HRID 920895 반응식
[Br-].[Br:2][CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][C:30]=1[CH:39]=O>C1COCC1>[Br:2]/[CH:3]=[CH:39]\[C:30]1[CH:31]=[CH:32][C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:29]=1

참가 물질

5

반응물 3

HCID 796192-QuinolinecarboxaldehydeHCID 2733422Phosphonium, (bromomethyl)triphenyl-, bromide (1:1)HCID 23665647Potassium tert-butoxide

생성물 1

HCID 15364160(Z)-2-(2-Bromovinyl)quinoline수율 59.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-70 °C

실험 절차

A suspension of 24.97 g (57.3 mmol) of (bromomethyl)triphenylphosphonium bromide in 160 mL of THF was chilled to −70° C. under argon. Then, 6.43 g (57.3 mmol) of potassium tert-butoxide were added portionwise and the suspension was allowed to stir at this temperature for 1 h. A solution of 7.5 g of (47.7 mmol) quinoline-2-carbaldehyde in 40 mL of THF was slowly added dropwise. The mixture was allowed to stir at −75° C. for further 5 hours and then warmed to room temperature overnight. 160 mL of PE were added. The precipitate formed was sucked off. The mother liquid was evaporated and the residue was stirred with diisopropyl ether. The residue formed was sucked off. Purification by chromatography (heptane/EA 3/1) yielded 6.6 g (59.1%) of the title compound.

후처리

  1. stirringto stir at −75° C. for further 5 hours
  2. temperaturewarmed to room temperature overnight
  3. addition160 mL of PE were added
  4. customThe precipitate formed
  5. customThe mother liquid was evaporated
  6. stirringthe residue was stirred with diisopropyl ether
  7. customThe residue formed
  8. customPurification by chromatography (heptane/EA 3/1)

출처 및 근거

ORD 기록
ord-610107384e8d4a35a8698cd063865337
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273068B2

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