62418-65-9 Usage
Uses
Used in Organic Synthesis:
3-Triethylsilyloxy-1,4-pentadiene is used as a masked vinyl ketone synthon for the preparation of various organic compounds through intramolecular Diels-Alder reactions. Its ability to form the 3-triethylsilyloxypentadienyl anion with sec-butyllithium enables a wide variety of electrophilic reactions, providing high selectivity and facilitating the synthesis of complex molecules.
Used in Pharmaceutical Industry:
3-Triethylsilyloxy-1,4-pentadiene is used as a precursor for the synthesis of pharmaceutical intermediates. Its reactivity and selectivity in intramolecular Diels-Alder reactions make it a valuable component in the development of new drugs and drug candidates.
Used in Chemical Research:
3-Triethylsilyloxy-1,4-pentadiene is utilized in chemical research for the study of intramolecular Diels-Alder reactions and the development of new synthetic methods. Its unique properties and reactivity contribute to the advancement of organic chemistry and the discovery of novel compounds with potential applications in various fields.
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 academic research and scientific papers
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.
3-Triethylsilyloxypentadienyllithium, a Versatile 1,3-Diene- or Vinyl ketone-Building Block
Oppolzer, Wolfgang,Snowden, Roger L.,Simmons, Dana P.
, p. 2002 - 2021 (2007/10/02)
Deprotonation of the 3-trialkylsilyloxy-1,4-diene 3a and subsequent electrophilic substitution of the non-isolated 3-trialkylsilyloxypentadienyllithium 4 gives the α- and γ-products 8 and/or 6 in good yields.Whereas alkylation of 4 proceeds with variable regioselectivity (Table 1) aldehydes and ketones attack preferentially the γ-position of 4 (Table 2).The desired γ-products 6 may be directly subjected to inter- and intramolecular -additions as demonstrated by the reactions 5a(=6d)-->7 and 6h-->19 (schemes 4 and 12).Alternatively, smooth fluoride-promoted silylether-cleavage 6-->11 (Scheme 8) provides a convenient approach to substituted vinyl ketones such as to the natural product 11f (Table 3).The stereoselective conversion 6k-->23 (Scheme 13) implies an endo-selective intramolecular Diels-Alder addition (26-->23) and exemplifies the use of 4 as an equivalent of the hypothetical anion IV.Furthermore, some electrophilic substitutions of the hexadienyllithium 15 have been studied (Scheme 10).
