Tributylstannane → HCID 53837129, compound

HRID 1074331Notes

Reaction equation

HRID 1074331 reaction equation
Br[C:2]1([F:19])[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>[F:19][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 53926002HCID 53926002, compound

Product 1

HCID 53837129HCID 53837129, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of ethyl 2-(2-bromo-2-fluorocyclopropyloxyimino)-3,3-ethylenedioxybutyrate (syn isomer)(4 g) and tri-n-butyltinhydride (2.28 ml) in benzene (30 ml) was refluxed under nitrogen atmosphere in the presence of 2,2'-azobisisobutyronitrile (250 mg) for 2 hours. The reaction mixture was concentrated in vacuo. The residue was subjected to column chromatography on silica gel and eluted with benzene. The fractions containing the compound, which had higher Rf-value on TLC [development solvent system: benzene], were collected and concentrated in vacuo to give ethyl 2-(2-fluorocyclopropyloxyimino)-3,3-ethylenedioxybutyrate (syn isomer)(1.36 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washeluted with benzene
  3. additionThe fractions containing the compound, which
  4. customwere collected
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76a7935565334b50973ac0587b2e2a1c
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

Loading…