((E)-3-IODO-1-METHYLPROPENYL)-TRIMETHYLSILANE
((E)-3-IODO-1-METHYLPROPENYL)-TRIMETHYLSILANE Basic information
- Product Name:
- ((E)-3-IODO-1-METHYLPROPENYL)-TRIMETHYLSILANE
- Synonyms:
-
- ((E)-3-IODO-1-METHYLPROPENYL)-TRIMETHYLSILANE
- 4-Iodobut-3-en-2-yl(trimethyl)silane
- Silane, [(1E)-3-iodo-1-methyl-1-propen-1-yl]trimethyl-
- CAS:
- 52685-51-5
- MF:
- C7H15ISi
- MW:
- 254.18
- Mol File:
- 52685-51-5.mol
((E)-3-IODO-1-METHYLPROPENYL)-TRIMETHYLSILANE Chemical Properties
- Boiling point:
- 188.9±23.0 °C(Predicted)
- Density
- 1.323±0.06 g/cm3(Predicted)
- solubility
- freely sol organic solvents.
((E)-3-IODO-1-METHYLPROPENYL)-TRIMETHYLSILANE Usage And Synthesis
Physical properties
bp 60 °C/20 mmHg.
Uses
(E)-1-Iodo-3-trimethylsilyl-2-butene can be used as annulation reagent; alkylative equivalent of 3-buten-2-one; 3-ketobutyl synthon.
Preparation
the first reported preparation of this reagent lacked full experimental details. The preparation given is a compilation of thework of several groups; the various steps have been selected to give optimum yields. 2-Propyn-1-ol is converted3 into its 3-(trimethylsilyl) derivative (1), which is then reduced4 using sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al). The intermediate vinylaluminum is reacted with iodine to produce the (Z)-iodoalkene (2). Treatment of this with lithium dimethylcuprate gives the allylic alcohol (3);. transformation into (E)-(3-chloro-1-methyl-1-propenyl)trimethylsilane (4) followed by halogen exchange with sodium iodide then gives reagent (5).