2,5-Dimethoxytetrahydrofuran → Methyl Benzoate

HRID 1060490Notes

Reaction equation

HRID 1060490 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](N)=[CH:6][C:5]=1Cl.COC1CCC(OC)O1>CC(O)=O.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

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

Product 1

HCID 7150Methyl Benzoate

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-adc2930492c8420ea25be3b2e2435cec
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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