Khellin → 1-(6-Hydroxy-4,7-dimethoxy-benzofuranyl)-3-(1-pyrrolidinyl)-2-buten-1-one

HRID 1278263

反応式

HRID 1278263 の反応式
CC1[O:19][C:7]2[C:8]([O:17][CH3:18])=[C:9]3[O:16][CH:15]=[CH:14][C:10]3=[C:11]([O:12][CH3:13])[C:6]=2C(=O)C=1.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>>[OH:19][C:7]1[CH:6]=[C:11]([O:12][CH3:13])[C:10]2[CH:14]=[C:15]([C:11](=[O:12])[CH:10]=[C:9]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH3:8])[O:16][C:9]=2[C:8]=1[O:17][CH3:18]

参加物

3

反応物 2

HCID 3828KhellinHCID 31268Pyrrolidine

生成物 1

HCID 542934601-(6-Hydroxy-4,7-dimethoxy-benzofuranyl)-3-(1-pyrrolidinyl)-2-buten-1-one収率 190.3%

実験手順

A methanolic solution of khellin (5.2 g) and pyrrolidine (2.82 g) is heated at 80° C. for 6 hr. Upon cooling, bright orange crystals precipitate from the reaction mixture. After filtration, there is obtained 6.3 g of pure title product. Silica gel TLC Rf is 0.74 in ethyl acetate. Infrared absorptions are observed at 3180, 3160, 3120, 2300, 1630, 1600, 1530, 1345, 1325, 1260, 1170, 1155, 1140, 1130, 1060, 1050, and 1030 cm-1. NMR absorptions are observed at 7.45, 6.8, 6.25, 4.05, 3.89, 3.22-3.70, 2.68, and 1.8-2.15δ. The mass spectrum exhibits peaks at 331, 300, 261, 220, 205, 177, 111, 110, 83, and 70. The carbon:hydrogen:nitrogen ratio is 65.09:6.32:4.18.

後処理

  1. temperatureUpon cooling
  2. custombright orange crystals precipitate from the reaction mixture
  3. filtrationAfter filtration

出典と根拠

ORDレコード
ord-39077099f27843f0a179ecdbf4081ff2
出典データセット
uspto-grants-1981_07
特許番号
US04281013

関連ノート

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