Water → Furo[2,3-b]pyridin-3-yl-acetic acid ethyl ester

HRID 1767064ノート

反応式

HRID 1767064 の反応式
[H-].[Na+].C[Si](C)(C)N[Si](C)(C)C.[O:12]1[C:16]2=[N:17][CH:18]=[CH:19][CH:20]=[C:15]2[C:14](=O)[CH2:13]1.[OH2:22].[O:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>>[CH2:24]([O:23][C:27](=[O:22])[CH2:26][C:14]1[C:15]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[O:12][CH:13]=1)[CH3:25]

参加物

6

反応物 5

HCID 962WaterHCID 8028Tetrahydrofuran2 回HCID 13838HexamethyldisilazaneHCID 24758Sodium hydrideHCID 125140462H,3H-furo(2,3-b)pyridin-3-one

生成物 1

HCID 10035840Furo[2,3-b]pyridin-3-yl-acetic acid ethyl ester

実験手順

To a suspension of 0.325 g (8.14 mmol) of sodium hydride (50% suspension in mineral oil) in 8 ml of anhydrous tetrahydrofuran was added 0.1 ml of 1,1,1,3,3,3-hexamethyldisilazane and 1.81 g (8.14 mmol) of triethyl phosphonoacetate (Aldrich) in 4 ml of anhydrous tetrahydrofuran. The resulting mixture was stirred at room temperature for 1 h, cooled at 0° C. and there was added 1 g (7.4 mmol) of furo[2,3-b]pyridin-3-one (prepared according to J. Het. Chem. 1986, 23, 1465–1469). After being stirred at room temperature for 24 h, water was added, the mixture was extracted with dichlomethane. The organic phase was dried and evaporated to give crude product, which was purified by silica gel chromatography, eluting with ethyl acetate/cyclohexane in the proportions 40/60 to give 0.73 g of pure product.

後処理

  1. temperaturecooled at 0° C.
  2. stirringAfter being stirred at room temperature for 24 h
  3. extractionthe mixture was extracted with dichlomethane
  4. customThe organic phase was dried
  5. customevaporated
  6. customto give crude product, which
  7. customwas purified by silica gel chromatography
  8. washeluting with ethyl acetate/cyclohexane in the proportions 40/60

出典と根拠

ORDレコード
ord-7295388289814990aa658db4bcb4e89b
出典データセット
uspto-grants-2007_06
特許番号
US07232827B2

反応ノート

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