Triethylamine → HCID 18319509, compound

HRID 1699374Notes

Reaction equation

HRID 1699374 reaction equation
[C-]#N.[K+].FC(F)(F)S(O[C:10]1[C:20]2[O:19][CH2:18][CH2:17][C:16]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)(=O)=O.[CH2:28]([N:30](CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Zn].Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O.C(OCC)(=O)C>[C:28]([C:10]1[C:20]2[O:19][CH2:18][CH2:17][C:16]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)#[N:30]

Participants

10

Reactant 4

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 11430Potassium CarbonateHCID 18319542HCID 18319542, compound

Product 1

HCID 18319509HCID 18319509, compound

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of zinc (69.2 mg, powder) and potassium cyanide (0.12 g) in N,N-dimethylformamide (10.5 ml) was stirred for 10 minutes under nitrogen atmosphere at ambient temperature and thereto was added successively ethyl 2,3-dihydro-9-trifluoromethanesulfonyloxy-1-benzoxepin-4-carboxylate (0.53 g), triethylamine (0.25 ml), and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium (0.12 g, complex with dichloromethane (1:1)). The reaction mixture was stirred at 60° C. for 2 hours. Thereto was added a mixture of ethyl acetate and water, basified by aqueous potassium carbonate, and filtered off. The organic layer was washed with 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 (1:9) to give a solid of ethyl 9-cyano-2,3-dihydro-1-benzoxepin-4-carboxylate (310 mg).

Workup

  1. stirringThe reaction mixture was stirred at 60° C. for 2 hours
  2. additionThereto was added
  3. filtrationfiltered off
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by medium pressure liquid chromatography (silica gel)
  8. additiona mixture of ethyl acetate and n-hexane (1:9)

Sources & evidence

ORD record
ord-c9a1caa78fa74dd9822e1914e85c6093
Source dataset
uspto-grants-2002_02
Patent number
US06346527B1

Reaction notes

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