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30th August 2013 @ 13:01

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Reaction information

*#Reaction file  
*Reaction file type CDX

To a stirring solution of 2-bromobenzaldehyde (1.85 g, 1.17 mL, 10.0 mmol), 1-pentyne (750 mg, 1.1 mL), CuI (100 mg, 0.50 mmol), triphenylphosphine (100 mg, 0.40 mmol) and Et3N (20 mL), bis-triphenylphosphinepalladium(II) chloride (100 mg, 0.14 mmol) was added dropwise.  The reaction was refluxed for 17 hours before quenching with a saturated solution of NaHCO3 (20.0 mL).  The product was extracted into diethyl ether (3 x 50 mL), the combiner organic layer washed with water (3 x 50 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure.  Column chromatography (SiO2, 0-100 % Et2O:petroleum) afforded the title compound as a red oil (9.00 g, 9.0 mmol, 90 %).

*Yield (%)  90
*Type of Yield Isolated product yield
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp130.pdf
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Overall reaction? True
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Attached Files
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp130.pdf