Tributylstannane → HCID 90910115, compound

HRID 449907Notes

Reaction equation

HRID 449907 reaction equation
[Cl:1][C:2]1(Cl)[CH2:4][CH:3]1[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C>>[Cl:1][C@@H:2]1[CH2:4][C@H:3]1[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

4

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 2780296HCID 2780296, compound

Product 1

HCID 90910115HCID 90910115, compoundYield 26.5%

Conditions

Temperature
90 °C

Procedure

A mixture of tert-butyl 2,2-dichlorocyclopropanecarboxylate (1.0 g, 4.7 mmol), tributyltin hydride (1.68 g, 5.7 mmol) and AIBN (50 mg) were heated to 90° C. for 1 h. The mixture was cooled to room temperature and distillation afforded a mixture of cis and trans t-butyl 2-chloro-1-cyclopropane carboxylate (220 mg, yield: 26%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. distillationdistillation
  3. customafforded

Sources & evidence

ORD record
ord-8e067f85fcbd4eaf84d0e86c9933aae8
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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