Tributylstannane → 1-Fluoro-3-(4-chlorophenyl)-3-methyl-1-tributylstannyl-1-butene

HRID 54267

Reaction equation

HRID 54267 reaction equation
[F:1][C:2](S(C1C=CC=CC=1)(=O)=O)=[CH:3][C:4]([CH3:13])([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)[CH3:5].[CH2:23]([SnH:27]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH3:26].N(C(C)(C)C#N)=NC(C)(C)C#N>C1CCCCC1>[F:1][C:2]([Sn:27]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([Cl:12])=[CH:10][CH:11]=1)([CH3:5])[CH3:13]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 538605131-Fluoro-1-phenylsulfonyl-3-methyl-3-(4-chlorophenyl)-1-butene

Product 1

HCID 676323451-Fluoro-3-(4-chlorophenyl)-3-methyl-1-tributylstannyl-1-butene

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Under a nitrogen atmosphere, a stirring solution of 22.7 grams (0.067 mole) of 1-fluoro-1-phenylsulfonyl-3-methyl-3-(4-chlorophenyl)-1-butene, 42.0 grams (0.14 mole) of tributyltin hydride, and 0.5 gram (catalyst) of azobisisobutyronitrile in 700 mL of cyclohexane is heated at reflux for about three hours. After this time the reaction mixture is cooled to ambient temperature, and 125 mL of silica gel is added. The mixture is concentrated under reduced pressure, and the residue is subjected to column chromatography. The product-containing fractions are combined and concentrated under reduced pressure, yielding 1-fluoro-3-(4-chlorophenyl)-3-methyl-1-tributylstannyl-1-butene.

Workup

  1. temperatureat reflux for about three hours
  2. addition125 mL of silica gel is added
  3. concentrationThe mixture is concentrated under reduced pressure
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-beee978054c2486f921e37cce4ee1d7b
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Linked notes

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