Sodium Carbonate → Methyl 5-(pyridin-4-yl)furan-2-carboxylate

HRID 278556

반응식

HRID 278556 반응식
Br[C:2]1[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][C:14](OB(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(OCC)(=O)C>[N:11]1[CH:16]=[CH:15][C:14]([C:2]2[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 599633Methyl 5-bromofuran-2-carboxylateHCID 218058124-Pyridylboric acid

생성물 1

HCID 22627954Methyl 5-(pyridin-4-yl)furan-2-carboxylate수율 17.2%

시약·촉매·용매 2

HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of methyl 5-bromo-2-furancarboxylate (820 mg), 4-pyridyl boric acid (500 mg), tetrakistriphenyl-phosphine palladium(0) (250 mg) in dimethoxyethane (15 ml) was added 2 M sodium carbonate solution (4 ml) and the solution was heated for 15 hours under reflux. The reaction solution was diluted with ethyl acetate, and the organic layer was separated, washed with water, extracted with 1 N hydrochloric acid. The extract was made alkaline with sodium hydroxide solution, extracted with ethyl acetate, dried and concentrated to give a colorless solid of methyl 5-(4-pyridyl)-2-furancarboxylate (126 mg). 1H-NMR (CDCl3) δ: 3.94 (3H, s), 6.96 (1H, d, J=3.8 Hz), 7.27 (1H, d, J=3.8 Hz), 7.64 (2H, d, J=6.2 Hz), 8.68 (2H, d, J=6.2 Hz). IR (KBr): 1727, 1608, 13.7, 1145 cm−1.

후처리

  1. temperaturethe solution was heated for 15 hours
  2. temperatureunder reflux
  3. customthe organic layer was separated
  4. washwashed with water
  5. extractionextracted with 1 N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. customdried
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0ad3fded4eb44ab9994f87ef46f42992
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359134B1

연결된 노트

불러오는 중…