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

HRID 1767064노트

반응식

HRID 1767064 반응식
[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]

참가 물질

6

반응물 5

HCID 962WaterHCID 8028Tetrahydrofuran2회HCID 13838HexamethyldisilazaneHCID 24758Sodium hydrideHCID 125140462H,3H-furo(2,3-b)pyridin-3-one

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7295388289814990aa658db4bcb4e89b
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07232827B2

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