Water → 2-Cyclopropanecarbonyl-7-methoxybenzofuran-4-carboxylic Acid 4-nitrophenyl Ester

HRID 1108311Notes

Reaction equation

HRID 1108311 reaction equation
[CH:1]1([C:4]([C:6]2[O:7][C:8]3[C:9](=[C:11]([C:17]([OH:19])=[O:18])[CH:12]=[CH:13][C:14]=3[O:15][CH3:16])[CH:10]=2)=[O:5])[CH2:3][CH2:2]1.[N+:20]([C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1)([O-:22])=[O:21].Cl.CN(C)CCCN=C=NCC.O>ClCCl.CN(C)C1C=CN=CC=1>[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([O:18][C:17]([C:11]2[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:8]3[O:7][C:6]([C:4]([CH:1]4[CH2:2][CH2:3]4)=[O:5])=[CH:10][C:9]=23)=[O:19])=[CH:25][CH:24]=1)([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 187848532-Cyclopropanecarbonyl-7-methoxybenzofuran-4-carboxylic Acid

Product 1

HCID 541277062-Cyclopropanecarbonyl-7-methoxybenzofuran-4-carboxylic Acid 4-nitrophenyl EsterYield 80.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2-cyclopropanecarbonyl-7-methoxybenzofuran-4-carboxylic acid (0.50 g) in dichloromethane (30 ml) under an atmosphere of nitrogen was added 4-nitrophenol (0.29 g), 4-dimethylaminopyridine (20 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.41 g). The reaction mixture was stirred at room temperature for 18 h. Water (30 ml) was added and the mixture extracted with dichloromethane (150 ml). The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 40% ethyl acetate in hexane afforded the title compound as a pale yellow solid (0.59 g).

Workup

  1. extractionthe mixture extracted with dichloromethane (150 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica eluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0ffbe286285745c8822697759a08e46d
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

Loading…