3-트리에틸실록시-1,4-펜타디엔

용도3-Triethylsilyloxy-1,4-pentadiene is used as a masked vinyl ketone synthon; a precursor for either the diene or dienophile in the intramolecular Diels–Alder reaction.) It may be used to prepare the useful 3-triethylsilyloxypentadienyl anion via metalation with sec-butyllithium (eq 1).A wide variety of electrophiles may be used and the selectivity is based on kinetics.The method has been used to prepare intermediates for intramolecular Diels–Alder reactions (eqs 4 and 5).

3-Triethylsilyloxy-1,4-pentadiene is by silylation of 3-hydroxy-1,4-pentadiene with chlorotriethylsilane.1,2 Other relatives of the title compound are available by silylation with chlorotrimethylsilane2 or t-butyldimethylchlorosilane3 3-Trimethylsilyloxy- 1,4-pentadiene is usually prepared and used in situ. Storage of 3-trimethylsilyl-1,4-pentadiene at 30°C is recommended. The dianion of the parent 3-hydroxy-1,4-pentadiene can also be prepared.