4-(Trimethylsilyl)-3-butyn-2-one

clear slightly yellow liquid

4-(Trimethylsilyl)-3-butyn-2-one (TMSB) has been used to investigate its asymmetric bioreduction to (S)-4-(trimethylsilyl)-3-butyn-2-ol {(S)-TMSBOL} by employing biocompatible water-immiscible ionic liquids (ILs). TMSB may be used for the synthesis of entecavir (BMS-200475).

4-(Trimethylsilyl)-3-butyn-2-one is a ketone. Its asymmetric bioreduction to enantiopure {(S)-TMSBOL in various hydrophilic ionic liquid (ILs) solvent systems has been reported.

Equipped with a thermometer, spherical condenser tube (the upper end of the connection of anhydrous calcium chloride drying tube and then pass into the NaOH aqueous solution) in a 100 ml three-necked bottle, according to a certain charging method, in accordance with a certain proportion of bis (trimethylsilyl) acetylene and methanol added to the reaction bottle, and constantly pass into the nitrogen to open the reaction, when the temperature rises to 60 ~ 80 , began to add acetyl chloride droplets, reaction of the resulting HCI from the continuous passage of nitrogen brought out by the condensation tube, in the drying tube by NaOH aqueous solution absorption, titration is complete, and then continue to reflux for a certain period of time until the reaction temperature is no longer elevated, stop the reaction, the reaction device was quickly converted to a decompression distillation extracted half an hour of the gas for the exclusion of residual trace HCI gas, and then converted to atmospheric distillation of the reaction device to collect the fractions of 185 or so, that is, the final The target product 4-trimethylsilyl-3-butyn-2-one (content higher than 97%).