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

HRID 2375342Notes

Reaction equation

HRID 2375342 reaction equation
[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]

Participants

6

Reactant 5

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

Product 1

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

Procedure

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 dichloromethane. 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.

Workup

  1. temperaturecooled at 0° C.
  2. stirringAfter being stirred at room temperature for 24 h
  3. extractionthe mixture was extracted with dichloromethane
  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

Sources & evidence

ORD record
ord-f94922b35170415ebd8770f5a0211c06
Source dataset
uspto-grants-2008_12
Patent number
US07465737B2

Reaction notes

Loading…