Potassium Carbonate → HCID 13849459, compound

HRID 978107Notes

Reaction equation

HRID 978107 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[O:11][C:12]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20]C(OC)=O)[C:13]=3[C:14]=2[CH3:15])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]1([NH:7][C:8]([C:10]2[O:11][C:12]3[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[C:13]=3[C:14]=2[CH3:15])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 20205108HCID 20205108, compound

Product 1

HCID 13849459HCID 13849459, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-phenyl-4-methoxycarbonyloxy-3-methylbenzofuran-2-carboxamide (328 mg, 1 mmole), methanol (1.5 m) and 10% potassium carbonate solution (1.5 ml) was stirred under argon overnight. After partial neutralization with acetic acid (0.06 ml) and evaporation to about 5 ml, water and ethyl acetate were added. The aqueous layer was extracted a second time with ethyl acetate and then acidified with, hydrochloric acid and extracted again. The combined ethyl acetate extract was washed with saturated sodium chloride solution, dried with MgSO4, and evaporated to a gum. Column chromatography of the latter (Merck silica gel eluted with 1:1:2 ethyl acetate/methylene chloride/hexane) gave 200 mg of product (80%).

Workup

  1. customAfter partial neutralization with acetic acid (0.06 ml) and evaporation to about 5 ml, water and ethyl acetate
  2. additionwere added
  3. extractionThe aqueous layer was extracted a second time with ethyl acetate
  4. extractionextracted again
  5. extractionThe combined ethyl acetate extract
  6. washwas washed with saturated sodium chloride solution
  7. dry with materialdried with MgSO4
  8. customevaporated to a gum
  9. washColumn chromatography of the latter (Merck silica gel eluted with 1:1:2 ethyl acetate/methylene chloride/hexane)

Sources & evidence

ORD record
ord-384779cfe3e94e78b030816987ff579a
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

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