62418-65-9 Usage
Physical properties
bp 140°C; n20D 1.4390.
Uses
3-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).
Preparation
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.
Purification Methods
Dissolve it in pentane, wash this with H2O, dry (Na2SO4), evaporate, and distil it under vacuum. RF values on Kieselgel 60 are 0.15 (pentane) and 0.60 (*C6H6). [IR, NMR, MS: Oppolzer et al. Helv Chim Acta 64 2002 1981.]
Check Digit Verification of cas no
The CAS Registry Mumber 62418-65-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,2,4,1 and 8 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 62418-65:
(7*6)+(6*2)+(5*4)+(4*1)+(3*8)+(2*6)+(1*5)=119
119 % 10 = 9
So 62418-65-9 is a valid CAS Registry Number.
62418-65-9Relevant articles and documents
The chemoselective and efficient deprotection of silyl ethers using trimethylsilyl bromide
Shah, Syed Tasadaque A.,Guiry, Patrick J.
experimental part, p. 2168 - 2172 (2009/02/01)
An efficient and chemoselective cleavage of silyl ethers (primary, secondary and aromatic) by using catalytic quantities of trimethylsilyl bromide (TMSBr) in methanol is reported. A wide range of alkyl silyl ethers such as TBS, TIPS, and TBDPS can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. The deprotection of silyl esters was also achieved employing catalytic quantities of TMSBr. The Royal Society of Chemistry 2008.
