Triethylamine → Ethyl 4-(2-methoxycarbonylvinyl)-3-nitrobenzoic acid

HRID 1712267Notes

Reaction equation

HRID 1712267 reaction equation
Cl[CH:2]([C:18]([O:20][CH3:21])=[O:19])[CH2:3][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][C:5]=1[N+:15]([O-:17])=[O:16].[CH2:22](N(CC)CC)[CH3:23]>O1CCCC1>[CH2:22]([C:6]1[C:5]([N+:15]([O-:17])=[O:16])=[C:4]([CH:3]=[CH:2][C:18]([O:20][CH3:21])=[O:19])[CH:14]=[CH:13][C:7]=1[C:8]([OH:10])=[O:9])[CH3:23]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 15091479Ethyl 4-(2-chloro-2-methoxycarbonylethyl)-3-nitrobenzoate

Product 1

HCID 68501280Ethyl 4-(2-methoxycarbonylvinyl)-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 3.20 g of ethyl 4-(2-chloro-2-methoxycarbonylethyl)-3-nitrobenzoate in 130 ml of tetrahydrofuran is admixed with 6.46 ml of triethylamine and stirred at reflux over 18 hours. The reaction mixture is cooled, poured onto water (300 ml) and extracted with tert-butyl methyl ether (2×300 ml). The organic phases are washed successively with water (2×300 ml) and brine (150 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The crude title compound is obtained as a slightly yellowish solid from the residue. Rf=0.30 (1:2 EtOAc-heptane). Rt=4.50.

Workup

  1. temperatureat reflux over 18 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water (300 ml)
  4. extractionextracted with tert-butyl methyl ether (2×300 ml)
  5. washThe organic phases are washed successively with water (2×300 ml) and brine (150 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-af588ccb59e74ceaafefe01be0891e3c
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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