Tributylstannane → HCID 53837129, compound

HRID 1723573Notes

Reaction equation

HRID 1723573 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-fluorocyclopropyloxy- imino)-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-d8c4e92c91ff4fee825ef8b4018d4f5f
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

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