4-Nitrophenol → (E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acid 4-nitrophenyl ester

HRID 1651272Notes

Reaction equation

HRID 1651272 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]2[C:7]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:8](/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])[O:9][C:5]=2[CH:4]=1.[N+:22]([C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)([O-:24])=[O:23].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([O:13][C:12](=[O:14])/[CH:11]=[CH:10]/[C:8]2[O:9][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:21]=[CH:20][C:6]=3[C:7]=2[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14742803(E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acid

Product 1

HCID 14742814(E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acid 4-nitrophenyl esterYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 113, (E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acid (3.35 g) was reacted with 4-nitrophenol (1.8 g) in dichloromethane (35 mL) in the presence of 1,3-dicyclohexylcarbodiimide (2.42 g). The crude product was crystallized from 2-propanol to afford 4.1 g of (E)-3-(6-methoxy-3-pentylbenzofuran-2-yl)-2-propenoic acid 4-nitrophenyl ester, mp 120°-121.5° C. Anal. Calcd for C23H23NO6 : C, 67.47; H, 5.66; N, 3.42 Found: C, 67.29; H, 5.89; N, 3.43

Workup

  1. customThe crude product was crystallized from 2-propanol

Sources & evidence

ORD record
ord-23fbb3adf32d4886915d87878e38c616
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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