Hydrochloric Acid → ethyl 3-amino-5-(furan-2-yl)-1H-pyrrole-2-carboxylate

HRID 1926017ノート

反応式

HRID 1926017 の反応式
CC1C=CC(S(O[C:12]([C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)=[CH:13][C:14]#[N:15])(=O)=O)=CC=1.Cl.[NH2:22][CH:23](C(OCC)=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25].[O-]CC.[Na+].Cl>C(O)C.O1CCCC1>[NH2:15][C:14]1[CH:13]=[C:12]([C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)[NH:22][C:23]=1[C:24]([O:26][CH2:27][CH3:28])=[O:25]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 3084143Propanedioic acid, 2-amino-, 1,3-diethyl ester, hydrochloride (1:1)HCID 545345202-Cyano-1-(2-furyl)vinyl 4-methylbenzenesulfonate

生成物 1

HCID 10751393ethyl 3-amino-5-(furan-2-yl)-1H-pyrrole-2-carboxylate収率 33.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-cyano-1-(2-furyl)vinyl 4-methylbenzenesulfonate (10.48 g) and diethyl aminomalonate hydrochloride (7.67 g) in a mixed solvent of ethanol (120 mL)-tetrahydrofuran (64 mL) was added dropwise a solution (36.9 mL) of 20% sodium ethoxide in ethanol under ice-cooling. After stirring at room temperature for 12 hrs, the reaction mixture was poured into ice water (350 mL) and adjusted to pH 7 with 1N hydrochloric acid. The organic solvent was evaporated under reduced pressure, and the residue was extracted with ethyl acetate (150 mL×3). The organic layers were combined, washed with saturated brine (100 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was purified by silica gel column chromatography (eluent, hexane:methyl acetate=3:1→1:1) and the obtained solid was recrystallized from ethyl acetate-hexane to give the title compound (2.66 g).

後処理

  1. temperaturecooling
  2. customThe organic solvent was evaporated under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate (150 mL×3)
  4. washwashed with saturated brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationAfter concentration under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent, hexane:methyl acetate=3:1→1:1)
  8. customthe obtained solid was recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-c991b851240c498ebf42d948d73e79a2
出典データセット
uspto-grants-2012_05
特許番号
US08178543B2

反応ノート

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