All Notebooks | Help | Support | About
30th August 2013 @ 14:35

This post is compatible for submission to ChemSpider Reactions.

See ChemSpider Reactions template - help and further information for help when using it.

Reaction information

*#Reaction file
ReactionScheme.cdx
 
*Reaction file type CDX 
*Procedure

To a solution of ZrCp2Cl2 (514 mg, 1.76 mmol) in THF (7 mL) under Ar at –80 °C was added dropwise n-butyllithium (1.40 mL of a 2.5 M solution in hexanes, 3.52 mmol). After 10 minutes, ((5-(4-pentenyloxy)-4-pentynyl)oxy)-(tert-butyl) dimethylsilane (280 mg, 1 mmol) was added. The solution was allowed to warm for 2 h, before addition of MeOH (1 mL) and NaHCO3 solution (2 mL). After stirring over night, the reaction mixture was poured into saturated NaHCO3 solution (10 mL) and pentane (15 mL). The aqueous layer was separated and extracted with pentane. The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated to provide the title compound as a pale yellow oil (286 mg, 1.00 mmol, 63%)

*Yield (%) 63
*Type of Yield Isolated Product Yield
Reference(s)
DavidOwenThesis2000pp37,95,96.pdf
210LABBOOK.JPG
Further information Compound 210: tert-Butyldimethyl((4-(3-methyltetrahydro-2H-2-pyranyliden)butyl)oxy) silane

For multistep reactions (or their steps):

Overall reaction? False
For overall reaction - links to child reaction steps N/A
For step in multistep reaction - link to previous reaction step Reaction 208
For step in multistep reaction - link to following reaction step N/A 
Attached Files
ReactionScheme.gif
ReactionScheme.cdx
DavidOwenThesis2000pp37,95,96.pdf
210LABBOOK.JPG