Dimethylformamide → HCID 18319504, compound

HRID 1699391Notes

Reaction equation

HRID 1699391 reaction equation
I[C:2]1[C:12]2[O:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.ClCCl.[C]=O.C([SiH](CC)CC)C.CN(C)[CH:31]=[O:32]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.C(OCC)(=O)C.C(N(CC)CC)C>[CH:31]([C:2]1[C:12]2[O:11][CH2:10][CH2:9][C:8]([C:13]([O:15][CH3:16])=[O:14])=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:32]

Participants

10

Reactant 5

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 12052TriethylsilaneHCID 18319526HCID 18319526, compoundHCID 178418416HCID 178418416, compound2×

Product 1

HCID 18319504HCID 18319504, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl 2,3-dihydro-9-iodo-1-benzoxepin-4-carboxylate (15 g) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (1.9 g) in N,N-dimethylformamide (225 ml) was introduced carbon monoxide for 15 minutes. To the mixture was added the triethylamine (15.8 ml) and triethylsilane (14.5 ml) and to the mixture was introduced carbon monoxide for 1hour. Additionally, the reaction mixture was stirred for 3 days at ambient temperature under carbon monoxide atmosphere. To the reaction mixture was added a mixture of ethyl acetate and water, and catalyst ws filtered off. The separated organic layer was washed with a water, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with a mixture of diisopropyl ether and hexane (1:1) to give methyl 2,3-dihydro-9-formyl-1-benzoxepin-4-carboxylate (7.7 g).

Workup

  1. additionTo the reaction mixture was added
  2. filtrationfiltered off
  3. washThe separated organic layer was washed with a water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was triturated with a mixture of diisopropyl ether and hexane (1:1)

Sources & evidence

ORD record
ord-dfd058cfe8614636b92adff89c821806
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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