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

HRID 1278263

반응식

HRID 1278263 반응식
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]

참가 물질

3

반응물 2

HCID 3828KhellinHCID 31268Pyrrolidine

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-39077099f27843f0a179ecdbf4081ff2
출처 데이터셋
uspto-grants-1981_07
특허 번호
US04281013

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