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29th August 2013 @ 15:27

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Reaction information

*#Reaction file  
*Reaction file type CDX

To a stirred solution, at –10 °C under argon, of 1-pentyne (9.86 mL, 0.10 mol) in THF (90 mL) nBuLi (44 mL, 2.5 M solution in hexanes, 0.11 mol) was added slowly.  After 10 minutes the resulting solution was cooled to –20 °C before addition of 1,3-dibromopropane (10.15 mL, 0.10 mol) followed by HMPA (17.4 mL, 0.10 mol).  The reaction was warmed to room temperature, stirred for 16 hours then quenched with a saturated solution of NaHCO3 (20.0 mL).  The product was extracted with diethyl ether (3 x 50 mL), the combined organic layer washed with water (3 x 50 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure to afford the crude product (estimated yield of title compound 45 % by NMR).  The crude product was used directly in subsequent reactions.

*Yield (%)  45
*Type of Yield NMR estimate
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp125.pdf
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Attached Files
DM Thesis_2000_pp51-59.pdf
DM Thesis_2000_pp125.pdf