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

HRID 269916

反応式

HRID 269916 の反応式
[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

参加物

5

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 231114661-(2,5-Difluoro-4-methoxyphenyl)piperidin-4-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0354f4e12ffe4f7cad2355f89c6f816a
出典データセット
uspto-grants-2008_11
特許番号
US07449466B2

関連ノート

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