4-Nitrophenol → HCID 14347448, compound

HRID 2232852Notes

Reaction equation

HRID 2232852 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[C:9](/[C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[CH:10]/[CH:11]=[CH:12]/[C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.[N+:21]([C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1)([O-:23])=[O:22].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([O:14][C:13](=[O:15])/[CH:12]=[CH:11]/[CH:10]=[C:9](/[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)\[C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[CH:26][CH:25]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14347277HCID 14347277, compound

Product 1

HCID 14347448HCID 14347448, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 115, (2E,4Z)-5-(4-methoxyphenyl)-5-(2-thienyl)-2,4-pentadienoic acid (1.76 g) and 4-nitrophenol (1 g) in 20 mL of dichloromethane was treated with 1,3-dicyclohexylcarbodiimide (1.24 g). The mixture was stirred at room temperature for 18 hours then, after the usual work up, the ester was crystallized from 2-propanol to yield 1.45 g of (2E,4Z)-5-(4-methoxyphenyl)-5-(2-thienyl)-2,4-pentadienoic acid 4-nitrophenyl ester, mp 113°-115° C. A sample was recrystallized from 2-propanol to give the analytical specimen, mp 114.5°-115.5° C.

Workup

  1. customafter the usual work up, the ester was crystallized from 2-propanol

Sources & evidence

ORD record
ord-794c6bb36b674199970d3780bf2a8c5e
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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