Tributylstannane → t-Butyl 4-(2-(2-cyano-1-cyclopentanon-3-yl)ethyl]benzoate

HRID 742305Notes

Reaction equation

HRID 742305 reaction equation
[C:1]([C:3]1[C:4](=[O:8])[CH2:5][CH2:6][CH:7]=1)#[N:2].N(C(C)(C)C#N)=NC(C)(C)C#N.C([SnH](CCCC)CCCC)CCC.Br[CH2:35][CH2:36][C:37]1[CH:49]=[CH:48][C:40]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[CH:39][CH:38]=1>C1C=CC=CC=1>[C:1]([CH:3]1[CH:7]([CH2:35][CH2:36][C:37]2[CH:49]=[CH:48][C:40]([C:41]([O:43][C:44]([CH3:46])([CH3:45])[CH3:47])=[O:42])=[CH:39][CH:38]=2)[CH2:6][CH2:5][C:4]1=[O:8])#[N:2]

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 10803033Tert-butyl 4-(2-bromoethyl)benzoateHCID 113893681-Cyclopentene-1-carbonitrile, 5-oxo-

Product 1

HCID 10470833t-Butyl 4-(2-(2-cyano-1-cyclopentanon-3-yl)ethyl]benzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

A solution of the 2-cyano-2-cyclopenten-1-one (2.41 g, 22.5 mmol) prepared in the Preparative Example 101 in anhydrous benzene and a solution of azobisisobutyronitrile (AIBN) (0.05 g, a catalytic amount) and tri-n-butyltin hydride (3.62 g, 12.4 mmol) in anhydrous benzene were simultaneously gradually dropped into a solution of t-butyl 4-(2-bromoethyl)benzoate (3.21 g, 11.3 mmol) prepared in the Preparative Example 104 in anhydrous benzene under reflux by heating. The obtained mixture was heated under reflux for about 20 minutes and distilled to remove the solvent. The residue was purified by silica gel column chromatography to give the objective compound. yield: 0.43 g

Workup

  1. temperatureunder reflux
  2. temperatureby heating
  3. temperatureThe obtained mixture was heated
  4. temperatureunder reflux for about 20 minutes
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue was purified by silica gel column chromatography
  8. customto give the objective compound

Sources & evidence

ORD record
ord-b187b075d5c044f780d0e7e4d8cf458c
Source dataset
uspto-grants-1996_09
Patent number
US05554615

Reaction notes

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