Formic Acid → 5-Ethoxycarbonylfuran-2-ylacetic acid

HRID 517327Notes

Reaction equation

HRID 517327 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([CH2:11]Cl)=[CH:9][CH:10]=1)=[O:5])[CH3:2].[I-].[K+].[CH:15]([OH:17])=[O:16]>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([CH2:11][C:15]([OH:17])=[O:16])=[CH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 4875Potassium IodideHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylate

Product 1

HCID 698426325-Ethoxycarbonylfuran-2-ylacetic acid

Reagents, catalysts & solvents 1

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-Catalyst

Conditions

Temperature
75 °C

Procedure

5-Chloromethyl-2-furancarboxylic acid ethyl ester (1.0 g, 5.3 mmol), potassium iodide (0.044 g, 0.27 mmol), and chloro(1,5-cyclooctadiene)rhodium(I) dimer (0.26 g, 0.53 mmol) were dissolved in formic acid (25 mL), and the mixture was stirred at 75° C. for 6 hours under a carbon monoxide atmosphere. The solvent was evaporated, and the residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The drying agent was filtered off, the solvent was evaporated, and the residue was purified by silica gel column chromatography to give the title compound (0.61 g).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d4044127998548c698cb29c9f07ac67e
Source dataset
uspto-grants-2015_08
Patent number
US09115107B2

Reaction notes

Loading…