Tributylvinyltin → HCID 59479245, compound

HRID 450778Notes

Reaction equation

HRID 450778 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-2baa953dedc3415c82e1123244baac69
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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