Tributylstannane → HCID 131719403, compound

HRID 440380Notes

Reaction equation

HRID 440380 reaction equation
C1([CH:7]2[C:12](=S(=O)=O)[CH:11]=[CH:10][CH:9]=[C:8]2[C:16](=[CH2:21])[C:17]([O:19][CH3:20])=[O:18])C=CC=CC=1.[CH2:22]([SnH:26]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25].N(C(C)(C)C#N)=NC(C)(C)C#N>C1CCCCC1>[C:8]1([C:16](=[CH:21][Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH3:25])[C:17]([O:19][CH3:20])=[O:18])[CH:7]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 867494882-Phenyl-3-sulfonlyphenyl-propenoic acid, methyl ester

Product 1

HCID 131719403HCID 131719403, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Combine 2-phenyl-3-sulfonlyphenyl-propenoic acid, methyl ester (41.0 g, 136 mmol) and tri-n-butyltin hydride (79.0 g, 271 mmol) in cyclohexane (900 mL). Add 2,2'-azobisisobutyronitrile (AIBN) (0.7 g, 4.3 mmol) and heat to reflux for 3 hours. Cool to ambient temperature and evaporate in vacuo. Chromatograph on silica gel eluting with 20% ethyl acetate/hexane. Evaporate the product containing fractions and chromatograph on silica gel eluting sequentially with 5% ethyl acetate/hexane and 10% ethyl acetate/hexane to give the title compound and a clear oil.

Workup

  1. temperatureto reflux for 3 hours
  2. customevaporate in vacuo
  3. customEvaporate the product
  4. additioncontaining fractions and chromatograph on silica gel eluting sequentially with 5% ethyl acetate/hexane and 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-43161b94fc1c4b48ad9972a48c9ce62a
Source dataset
uspto-grants-1996_05
Patent number
US05519048

Reaction notes

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