Water → 8-(p-Pentylcinnamoyl)amino-1,4-benzodioxane-2-acetic acid methyl ester

HRID 2165082Notes

Reaction equation

HRID 2165082 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:12]1[CH:30]=[CH:29][C:15]([CH:16]=[CH:17][C:18]([NH:20][C:21]2[CH:27]=[CH:26][CH:25]=[C:23]([OH:24])[C:22]=2[OH:28])=[O:19])=[CH:14][CH:13]=1)[CH2:8][CH2:9][CH2:10][CH3:11].[CH3:31][O:32][C:33](=[O:38])[CH:34]=[CH:35][CH2:36]Br.O>CC(C)=O>[CH3:31][O:32][C:33](=[O:38])[CH2:34][CH:35]1[O:28][C:22]2[C:21]([NH:20][C:18](=[O:19])[CH:17]=[CH:16][C:15]3[CH:14]=[CH:13][C:12]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:30][CH:29]=3)=[CH:27][CH:26]=[CH:25][C:23]=2[O:24][CH2:36]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 14229Methyl 4-bromobut-2-enoateHCID 542110523-(p-Pentylcinnamoyl)aminopyrocatechol

Product 1

HCID 539083158-(p-Pentylcinnamoyl)amino-1,4-benzodioxane-2-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (509 mg) was added to a solution of 3-(p-pentylcinnamoyl)aminopyrocatechol (300 mg; synthesized by the same procedure as reference example 1) and 4-bromo-2-butenoic acid methyl ester in acetone (10 ml), and the mixture was refluxed for 10 min. The reaction mixture was poured into water. The mixture was extracted with ethyl acetate. The extract was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1) to give the title compound (341 mg).

Workup

  1. temperaturethe mixture was refluxed for 10 min
  2. extractionThe mixture was extracted with ethyl acetate
  3. customThe extract was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-79cbd2214f834f12adc1723dd2023c0b
Source dataset
uspto-grants-1990_07
Patent number
US04939141

Reaction notes

Loading…