Methanol → Methyl 5-(4-chlorophenyl)furan-2-carboxylate

HRID 383143Notes

Reaction equation

HRID 383143 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([OH:15])=[O:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:16]O>OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 7266935-(4-Chlorophenyl)-2-furoic acid

Product 1

HCID 11564928Methyl 5-(4-chlorophenyl)furan-2-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
50 °C

Procedure

To a solution of 5-(4-chlorophenyl)-2-furoic acid (5.0 g, 22 mmol) in MeOH (50 mL) was added conc. H2SO4 (4 drops) and the resulting solution heated to 50° C. for 4 days. The reaction was cooloed and concentrated in vacuo. The residue was taken up in EtOAc (100 mL) and washed with saturated aqueous NaHCO3 (2×20 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by flash cjromatography (hexane/EtOAc 19:1) to give 3.8 g (72%) of a cream powder; MS m/z 254 (M++18, 100).

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with saturated aqueous NaHCO3 (2×20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash cjromatography (hexane/EtOAc 19:1)

Sources & evidence

ORD record
ord-78c06ffefe3741deb483844602ceea93
Source dataset
uspto-grants-2001_10
Patent number
US06310095B1

Reaction notes

Loading…