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Riedel-de Haen AG
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CAS:62418-65-9
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SIGMA-RBI
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800 736 3690 (Orders) |
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| | 3-TRIETHYLSILOXY-1,4-PENTADIENE Basic information |
| Product Name: | 3-TRIETHYLSILOXY-1,4-PENTADIENE | | Synonyms: | 3-TRIETHYLSILOXY-1,4-PENTADIENE;3-(triethylsilyloxy)-1,4-pentadiene;1,4-Pentadien-3-yloxy-triethylsilane;Silane, [(1-ethenyl-2-propen-1-yl)oxy]triethyl- | | CAS: | 62418-65-9 | | MF: | C11H22OSi | | MW: | 198.38 | | EINECS: | | | Product Categories: | | | Mol File: | 62418-65-9.mol |  |
| | 3-TRIETHYLSILOXY-1,4-PENTADIENE Chemical Properties |
| Boiling point | 74-75 °C/14 mmHg | | refractive index | n20/D 1.439 | | Fp | 58 °C | | storage temp. | 2-8°C | | solubility | sol pentane, benzene, THF, ether, CH2Cl2. |
| Safety Statements | 23-24/25 | | RIDADR | 1993 | | HazardClass | 3.2 | | PackingGroup | III |
| | 3-TRIETHYLSILOXY-1,4-PENTADIENE Usage And Synthesis |
| 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.] |
| | 3-TRIETHYLSILOXY-1,4-PENTADIENE Preparation Products And Raw materials |
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