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

HRID 1278263

Reaction equation

HRID 1278263 reaction equation
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]

Participants

3

Reactant 2

HCID 3828KhellinHCID 31268Pyrrolidine

Product 1

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

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-39077099f27843f0a179ecdbf4081ff2
Source dataset
uspto-grants-1981_07
Patent number
US04281013

Linked notes

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