18-Crown-6 → 1-(2-Butenyl)-7-(4-fluorobenzyloxy)-2,3-dimethylpyrrolo[2,3-d]pyridazine

HRID 1107735노트

반응식

HRID 1107735 반응식
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=1.C1OCCOCCOCCOCCOCCOC1.[CH2:34]([N:38]1[C:42]2=[C:43](Cl)[N:44]=[N:45][CH:46]=[C:41]2[C:40]([CH3:48])=[C:39]1[CH3:49])[CH:35]=[CH:36][CH3:37]>O1CCCC1>[CH2:34]([N:38]1[C:42]2=[C:43]([O:13][CH2:12][C:11]3[CH:14]=[CH:15][C:8]([F:7])=[CH:9][CH:10]=3)[N:44]=[N:45][CH:46]=[C:41]2[C:40]([CH3:48])=[C:39]1[CH3:49])[CH:35]=[CH:36][CH3:37]

참가 물질

6

반응물 4

HCID 2855718-Crown-6HCID 680224-Fluorobenzylic alcoholHCID 23665647Potassium tert-butoxideHCID 537196241-(2-Butenyl)-7-chloro-2,3-dimethylpyrrolo[2,3-d]pyridazine

생성물 1

HCID 539969541-(2-Butenyl)-7-(4-fluorobenzyloxy)-2,3-dimethylpyrrolo[2,3-d]pyridazine수율 63.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

0.85 g (0.0076 mole) of potassium tert-butoxide was added to a solution of 0.48 g-(0.0038 mole) of 4-fluorobenzyl alcohol and 0.08 g (0.0003 mole) of 18-crown-6 in 30 ml of tetrahydrofuran and the mixture was stirred at room temperature for 10 minutes. 0.45 g (0.0019 mole) of 1-(2-butenyl)-7-chloro-2,3-dimethylpyrrolo[2,3-d]pyridazine was then added to the mixture and stirred at room temperature for 8 hours. After completion of the reaction, the reaction mixture was poured into ice-water and the aqueous mixture was extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel using a 4:1 mixture of toluene and ethyl acetate as an eluent. An oily material thus obtained was crystallized in hexane to give 0.39 g of 1-(2-butenyl)-7-(4-fluorobenzyloxy)-2,3-dimethylpyrrolo[2,3-d]pyridazine (cis/trans=13/87) as a pale brown powder.

후처리

  1. stirringstirred at room temperature for 8 hours
  2. customAfter completion of the reaction
  3. extractionthe aqueous mixture was extracted with dichloromethane
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel using
  7. additiona 4:1 mixture of toluene and ethyl acetate as an eluent
  8. customAn oily material thus obtained
  9. customwas crystallized in hexane

출처 및 근거

ORD 기록
ord-95641fdf7231455cac3415e881af0be1
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06063782

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