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

HRID 278556

反応式

HRID 278556 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0ad3fded4eb44ab9994f87ef46f42992
出典データセット
uspto-grants-2002_03
特許番号
US06359134B1

関連ノート

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