Dimethylformamide → HCID 18319645, compound

HRID 1699379Notes

Reaction equation

HRID 1699379 reaction equation
I[C:2]1[CH:3]=C[C:5]2[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][C:6]=2[CH:17]=1.C(N([CH2:23][CH3:24])CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=[O:55].CN(C)[CH:58]=[O:59]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:58][O:59][C:3]([C:2]1[CH:17]=[CH:6][C:5]2[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][C:24]=2[CH:23]=1)=[O:55]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 18319538HCID 18319538, compoundHCID 178418416HCID 178418416, compound2×

Product 1

HCID 18319645HCID 18319645, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

To a mixture of ethyl 2,3-dihydro-7-iodo-1-benzoxepin-4-carboxylate (0.69 g), triethylamine (1.12 ml), 1,3-bis(diphenylphosphino)propane (0.165 g), and palladium(II) acetate (90 mg) in N,N-dimethylformamide (6.4 ml) was introduced carbon monoxide for 30 minutes. The reaction mixture was stirred for 5 hours at 95° C. in an atmosphere of carbon monoxide and partitioned between ethyl acetate and water. The organic layer was washed successively with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by medium pressure liquid chromatography (silica gel) using a mixture of ethyl acetate and n-hexane (1:4) to give a solid of ethyl 2,3-dihydro-7-methoxycarbonyl-1-benzoxepin-4-carboxylate (0.45 g).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by medium pressure liquid chromatography (silica gel)
  6. additiona mixture of ethyl acetate and n-hexane (1:4)

Sources & evidence

ORD record
ord-6c8dfa2f6f9543c08c9ce9a6575b5e5d
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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