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

HRID 868538Notes

Reaction equation

HRID 868538 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-bb79f03aa1494d29bb85f28c63eade35
Source dataset
uspto-grants-1988_10
Patent number
US04780469

Reaction notes

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