Potassium Carbonate → HCID 4378040, compound

HRID 2284853Notes

Reaction equation

HRID 2284853 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][O:23][C:24]([C:26]1[O:27][C:28]([CH2:31]Cl)=[CH:29][CH:30]=1)=[O:25]>CN(C=O)C>[C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:31][C:28]2[O:27][C:26]([C:24]([O:23][CH3:22])=[O:25])=[CH:30][CH:29]=2)=[CH:15][CH:14]=1)(=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143474-HydroxybenzophenoneHCID 75065Methyl 5-(chloromethyl)-2-furoate

Product 1

HCID 4378040HCID 4378040, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-hydroxybenzophenone (198.2 mg, 1.0 mmol) in DMF (3 mL) at 0° C. under nitrogen was added potassium carbonate (207 mg, 1.5 mmol) followed by methyl-5-chloromethyl-2-furoate (175 mg, 1.0 mmol). The reaction was allowed to warm to room temperature and the mixture was stirred at room temperature for 24 h. The reaction mixture was partitioned between water and ethyl acetate. The aqueous phase was extracted twice with ethyl acetate and the combined organic phases were washed with 10% aqueous K2CO3 solution, water, brine, dried over MgSO4, filtered and the solvent removed in vacuo to yield the title compound (330 mg, 98.2%) as a yellow oil.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. extractionThe aqueous phase was extracted twice with ethyl acetate
  3. washthe combined organic phases were washed with 10% aqueous K2CO3 solution, water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-205a1ec51c1447bfb3040e3fc4fe54e7
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

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