Tributylstannane → Ethyl 2-(2-chlorocyclopropyloxyimino)-3,3-ethylenedioxybutyrate

HRID 1074330Notes

Reaction equation

HRID 1074330 reaction equation
[Cl:1][C:2]1(Cl)[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>C1(C)C=CC=CC=1>[Cl:1][CH:2]1[CH2:4][CH:3]1[O:5][N:6]=[C:7]([C:13]1([O:15][CH2:16][CH2:17][O:18]1)[CH3:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 53818524HCID 53818524, compound

Product 1

HCID 54085048Ethyl 2-(2-chlorocyclopropyloxyimino)-3,3-ethylenedioxybutyrateYield 33.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 2-(2,2-dichlorocyclopropyloxyimino)-3,3-ethylenedioxybutyrate (syn isomer)(312 mg) and tri-n-butyltinhydride (0.55 ml) in toluene (2 ml) was refluxed under nitrogen atmosphere in the presence of catalytic amount of 2,2'-azobisisobutyronitrile for 2 hours. The reaction mixture was concentrated in vacuo. The residue was subjected to column chromatography on silica gel (24 g) and eluted with a mixture of diethyl ether and n-hexane (1:2 V/V). The fractions containing the compound, which had higher Rf-value on TLC [development solvent system: diethyl ether and n-hexane (2:1 V/V)], were collected and concentrated in vacuo to give ethyl 2-(2-chlorocyclopropyloxyimino)-3,3-ethylenedioxybutyrate (syn isomer)(94 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washeluted with a mixture of diethyl ether and n-hexane (1:2 V/V)
  3. additionThe fractions containing the compound, which
  4. customwere collected
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0976c6e08e6144738dba0b8f70d2efdc
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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