Potassium Carbonate → HCID 18319626, compound

HRID 1699375Notes

Reaction equation

HRID 1699375 reaction equation
I[C:2]1[C:12]2[O:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:18](=O)([O-:20])[O-:19].[K+].[K+].[C]=O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:18]([C:2]1[C:12]2[O:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)([OH:20])=[O:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18319552HCID 18319552, compoundHCID 178418416HCID 178418416, compound2×

Product 1

HCID 18319626HCID 18319626, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 2,3-dihydro-9-iodo-1-benzoxepin-4-carboxylate (5.62 g), potassium carbonate (9.03 g), and palladium(II) acetate (0.73 g) in aqueous N,N-dimethylformamide (48 ml, 67% v/v) was introduced carbon monoxide for 30 minutes. The reaction mixture was stirred for 2 days at ambient temperature in an atmosphere of carbon monoxide and partitioned between ethyl acetate and water. The aqueous layer was acidified with 1H hydrochloric acid and extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium thiosulfate and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give a solid of ethyl 9-carboxy-2,3-dihydro-1-benzoxepin-4-carboxylate (3.8 g).

Workup

  1. custompartitioned between ethyl acetate and water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with saturated aqueous sodium thiosulfate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-43365b17012d47c38f175afee4da0876
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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