Tributylstannane → HCID 53725137, compound

HRID 1723571Notes

Reaction equation

HRID 1723571 reaction equation
Br[C:2]1(Br)[CH2:4][CH:3]1[O:5][N:6]=[C:7]([C:13]1([O:18][CH2:17][CH2:16][O:15]1)[CH3:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[CH:3]1([O:5][N:6]=[C:7]([C:13]2([O:15][CH2:16][CH2:17][O:18]2)[CH3:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:2]1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 53766880HCID 53766880, compound

Product 1

HCID 53725137HCID 53725137, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of ethyl 2-(2,2-dibromocyclopropyloxyimino)-3,3-ethylenedioxybutyrate (syn isomer)(16.4 g) in benzene (300 ml) was dropwise added tri-n-butyltin hydride (33 ml). To the mixture was added 2,2'-azobisisobutyronitrile (0.5 g) and the resulting mixture was refluxed for 2 hours under nitrogen atmosphere. The mixture was concentrated in vacuo and the residue was subjected to column chromatography on silica gel using a mixture of chloroform and ethyl acetate (4:1 V/V) as an eluent to give ethyl 2-cyclopropyloxyimino-3,3-ethylenedioxybutyrate (syn isomer)(10.36 g) as an oil.

Workup

  1. temperaturethe resulting mixture was refluxed for 2 hours under nitrogen atmosphere
  2. concentrationThe mixture was concentrated in vacuo
  3. additiona mixture of chloroform and ethyl acetate (4:1 V/V) as an eluent

Sources & evidence

ORD record
ord-382b946e44704ead8382833a87adac21
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

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