3-Hydroxypyridine → Tert-butyl 2-(pyridin-3-yl)oxypropionate

HRID 2246481노트

반응식

HRID 2246481 반응식
[H-].[Na+].[OH:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.Br[CH:11]([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(=O)(O)[O-].[Na+]>CN(C=O)C>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH:11]([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]=1

참가 물질

6

반응물 4

HCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 545327tert-Butyl 2-bromopropanoate

생성물 1

HCID 22668079Tert-butyl 2-(pyridin-3-yl)oxypropionate수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To a suspension of 1.20 g of sodium hydride (60% oil dispersion; 30.0 mmol) in 10 mL of dry DMF at room temperature were added dropwise 2.85 g of 3-hydroxypyridine (30 mmol) in 10 mL of dry DMF, maintaining the temperature below 40° C., and the mixture was stirred at room temperature for 90 min. Under ice-cooling, 6.28 g of tert-butyl 2-bromopropionate (30 mmol) in 10 mL of dry DMF were slowly added dropwise, maintaining the inner temperature within 5 to 10° C., and then the mixture was warmed to room temperature with stirring for 4 hours. After neutralizing with saturated sodium bicarbonate aq., the mixture was extracted with ethyl acetate. The organic layer was washed with water and then saturated brine, dried and evaporated. The residue was purified by column chromatography on silica gel (eluent: n-hexane:ethyl acetate=2:1) to give 4.15 g of tert-butyl 2-(pyridin-3-yl)oxypropionate (Yield: 62%) as a brown oil.

후처리

  1. temperaturemaintaining the temperature below 40° C.
  2. temperatureUnder ice-cooling
  3. temperaturemaintaining the inner temperature within 5 to 10° C.
  4. temperaturethe mixture was warmed to room temperature
  5. stirringwith stirring for 4 hours
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialsaturated brine, dried
  9. customevaporated
  10. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-09239d5eceb24fe280a73de4d8c3d85c
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687525B2

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