Sodium hydride → 1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylideneacetonitrile

HRID 2389903ノート

反応式

HRID 2389903 の反応式
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH2:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]3[CH2:25][CH2:24][C:23](=O)[C:21]3=2)[O:16][CH2:15]1>O1CCCC1.C(=O)([O-])O.[Na+]>[CH2:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]3[CH2:25][CH2:24][C:23](=[CH:5][C:3]#[N:4])[C:21]3=2)[O:16][CH2:15]1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 591793681,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one

生成物 1

HCID 666019131,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-ylideneacetonitrile収率 91%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 516892Sodium Bicarbonate溶媒

実験手順

To a suspension of 60% sodium hydride (137 mg, 3.42 mmol) in tetrahydrofuran (15 mL) was added diethyl cyanomethylphosphonate (600 μL, 3.71 mmol) under ice-cooling, and the mixture was stirred for 15 min. A solution of 1,2,6,7-tetrahydro-8H-cyclopenta[d]furo[2,3-b]pyridin-8-one (500 mg, 2.85 mmol) in tetrahydrofuran (15 mL) was added thereto, and the mixture was further stirred for 15 min. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20) to give the title compound (514 mg, yield 91%).

後処理

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 15 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20)

出典と根拠

ORDレコード
ord-bf81db4e8dfe44478c66e290c7ac3258
出典データセット
uspto-grants-2012_09
特許番号
US08273761B2

反応ノート

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