Tributylvinyltin → HCID 59479245, compound

HRID 1747055Notes

Reaction equation

HRID 1747055 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1.[CH:9]([Sn](CCCC)(CCCC)CCCC)=[CH2:10]>C1(C)C=CC=CC=1>[CH:9]([C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1)=[CH2:10]

Participants

4

Reactant 2

HCID 81998TributylvinyltinHCID 877924-Bromothiophene-2-carbaldehyde

Product 1

HCID 59479245HCID 59479245, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5.0 g of 4-bromothiophene-2-carbaldehyde, 11.4 ml of vinyltributyltin, and 3.6 g of tetrakistriphenylphosphine palladium in 100 ml of toluene was heated at 110° C. for 4 hours under a sealed tube condition. The organic layer was extracted with ethyl acetate and washed with water. In addition, the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain 3.4 g of 4-vinylthiophene-2-carbaldehyde as a brown liquid.

Workup

  1. extractionThe organic layer was extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialIn addition, the organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-10c895300f7d479da38180a735470147
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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