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9th August 2013 @ 14:09
This post is compatible for submission to ChemSpider Reactions. See [blog=44639]ChemSpider Reactions template - help and further information[/blog] for help when using it. Reaction information *#Reaction file [data]28966[/data] *Reaction file type CDX *Procedure To a stirred suspension of Cp2ZrHCl (0.258 g, 1.0 mmol) in dry THF (10 mL) at RT was added neat 1-octene (0.125 mL, 0.8 mmol) dropwise over 3 minutes. After stirring the yellow solution for 1 h at RT, the reaction mixture was cooled to –78 C and a solution of the non-1-yn-3-yl benzensulfonate (0.294 g, 1.0 mmol) in dry THF (1 mL) was added dropwise followed by dropwise addition of freshly prepared LiTMP, [prepared from freshly distilled 2,2,6,6-tetramethylpiperidine (0.17 mL, 1.0 mmol) in dry THF (2 mL) and n-BuLi (0.4 mL of a 2.5 M solution in hexanes, 1.0 mmol) at –5 C over 15 min]. The stirring was continued for a further 1.5 h during which time the reaction mixture was allowed to warm to RT. The reaction mixture was re-cooled to –78 C and a solution of acetone (0.22 mL 3.0 mmol) in dry THF (1 mL) was added, the reaction mixture warmed gradually to RT. The reaction mixture was then refluxing for 20 h before cooling to RT and quenching with MeOH (5 mL) and a saturated aqueous solution of NaHCO3 (6 mL), the mixture left stirring overnight. The mixture was poured onto H2O (100 mL), the products extracted with Et2O (3 × 75 mL). The combined organic phases were washed with H2O (2 × 100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo to give the crude product as a yellow oil. Purification of the crude material by column chromatography on SiO2 (230 – 400 mesh) with hexane : EtOAc (10 : 1) as the eluent to yield the title compound as a yellow oil in yield of 0.118 g (50%, contained 10% of unidentified by-products). *Yield (%) 50 *Type of Yield Isolated product yield Reference(s) [data]28936[/data]; [data]28938[/data] Further information Characterisation of rac-3-Hexyl-2-methyltridec-4-yn-2-ol (4.82d) For multistep reactions (or their steps): Overall reaction?   For overall reaction - links to child reaction steps   For step in multistep reaction - link to previous reaction step   For step in multistep reaction - link to following reaction step