Water → HCID 13769242, 화합물

HRID 2232544노트

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HRID 2232544 반응식
[H-].[Na+].[C:3]([O:11]CC)(=[O:10])[CH2:4][C:5](OCC)=O.BrC[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:17]=1.O>O1CCCC1>[C:26]1([C:18]2[N:17]=[C:16]([CH2:5][CH2:4][C:3]([OH:11])=[O:10])[C:25]3[C:20]([CH:19]=2)=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 13769241HCID 13769241, 화합물

생성물 1

HCID 13769242HCID 13769242, 화합물수율 44.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
20 °C

실험 절차

Sodium hydride (6.5 g, 80% strength in oil) is placed with tetrahydrofuran (160 cc) under nitrogen, and a solution of diethyl malonate (34.9 g) in anhydrous tetrahydrofuran (200 cc) is added dropwise. After 1 hour's stirring at room temperature (approximately 20° C.), a solution of 1-bromomethyl-3-phenylisoquinoline (16.2 g) in anhydrous tetrahydrofuran (200 cc) is added. After 20 hours' stirring at 20° C., water (200 cc) is added and the aqueous phase extracted with ethyl acetate. The organic phase is dried and evaporated to dryness under reduced pressure. The residual product is chromatographed on silica gel with a cyclohexane/ethyl acetate (8:2 by volume) mixture as eluant. The product (11.5 g) is recovered, taken up in concentrated hydrochloric acid (115 cc) and brought to boiling for 20 hours. Water (200 cc) is added, and the precipitate is filtered off and washed with water and acetone. 3-Phenyl-1-isoquinolinepropanoic acid (6.7 g) m.p. 160° C., is obtained.

후처리

  1. stirringAfter 20 hours' stirring at 20° C.
  2. extractionthe aqueous phase extracted with ethyl acetate
  3. customThe organic phase is dried
  4. customevaporated to dryness under reduced pressure
  5. customThe residual product is chromatographed on silica gel with a cyclohexane/ethyl acetate (8:2 by volume) mixture as eluant
  6. customThe product (11.5 g) is recovered
  7. waitto boiling for 20 hours
  8. additionWater (200 cc) is added
  9. filtrationthe precipitate is filtered off
  10. washwashed with water and acetone

출처 및 근거

ORD 기록
ord-b2ec8e8746f1430b989b985bb3f189e4
출처 데이터셋
uspto-grants-1988_11
특허 번호
US04788204

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