Tetrahydrofuran → 1-(2,5-Difluoro-4-methoxyphenyl)-4-methoxymethylenepiperidine

HRID 269916

반응식

HRID 269916 반응식
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.[F:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[C:33]([F:38])=[CH:32][C:31]=1[N:39]1[CH2:44][CH2:43][C:42](=O)[CH2:41][CH2:40]1>O>[F:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[C:33]([F:38])=[CH:32][C:31]=1[N:39]1[CH2:44][CH2:43][C:42](=[CH:2][O:3][CH3:4])[CH2:41][CH2:40]1

참가 물질

5

반응물 3

HCID 8028Tetrahydrofuran2회HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 231114661-(2,5-Difluoro-4-methoxyphenyl)piperidin-4-one

생성물 1

HCID 231114001-(2,5-Difluoro-4-methoxyphenyl)-4-methoxymethylenepiperidine수율 34.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A reaction vessel was charged with methoxymethyltriphenyl-phosphonium chloride (1.114 g), the atomosphere indide the vessel was substituted with nitrogen, and anhydrous tetrahydrofuran (2 mL) was added, followed by further dropwise addition of 1.57 M n-butyl lithium-in-hexane solution (2 mL) at room temperature and thereafter 10 minutes' stirring at room temperature. To the reaction mixture a mixture of 1-(2,5-difluoro-4-methoxyphenyl)piperidin-4-one (676 mg) and anhydrous tetrahydrofuran (0.5 mL) was added dropwise, followed by 30 minutes' stirring at room temperature. To the reaction mixture water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous sodium sulfate. Distilling the solvent off, the crude product as obtained was purified on silica gel column chromatography (eluent, hexane: ethyl acetate=10:1) to provide 1-(2,5-difluoro-4-methoxyphenyl)-4-methoxymethylenepiperidine (257 mg).

후처리

  1. additionwas added
  2. additionwas added dropwise
  3. waitfollowed by 30 minutes
  4. stirring' stirring at room temperature
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated saline solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationDistilling the solvent off, the crude product
  9. customas obtained
  10. customwas purified on silica gel column chromatography (eluent, hexane: ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-0354f4e12ffe4f7cad2355f89c6f816a
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449466B2

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