2,5-Dimethoxytetrahydrofuran → 2-Chloro-4-(1-pyrrolyl)benzoic acid methyl ester

HRID 24717

Reaction equation

HRID 24717 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][C:5]=1[Cl:11].CO[CH:15]1[CH2:19][CH2:18][CH:17](OC)O1>CC(O)=O.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:15]=[CH:19][CH:18]=[CH:17]2)=[CH:6][C:5]=1[Cl:11]

Participants

5

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 11839197Methyl 4-Amino-2-chlorobenzoate

Product 1

HCID 47637352-Chloro-4-(1-pyrrolyl)benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 4-amino-2-chlorobenzoic acid methyl ester (0.46 g) and 2,5-dimethoxytetrahydrofuran (0.33 mL) in AcOH (16 mL) was heated under reflux for 2 h. The mixture was cooled to room temperature, diluted with water and extracted with EtOAc. The extract was washed with satd. NaHCO3 and brine, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexane/EtOAc 5/1) to yield 0.48 g of 2-chloro-4-(1-pyrrolyl)benzoic acid methyl ester. ESMS: m/z 236 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. extractionextracted with EtOAc
  4. washThe extract was washed with satd
  5. dry with materialNaHCO3 and brine, dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (silica gel; eluent: hexane/EtOAc 5/1)

Sources & evidence

ORD record
ord-7d9c216325c049cd98f689b70dd37e81
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Linked notes

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