I am running a reaction of Tmob-Teg-OH, Tmob being the protecting group. I want to convert the OH to Ts but am having problems. Any suggestions on improving the yield of the Tosylation? I am currently at 35%. The reaction is carried out under R.T. I am using 2N NaOH as my base and THF as my solvent. I have tried gently heating the rxn to 50 C and it doesn't seem to be helping. Any higher temperature leads to product breakdown.
Report to moderator 130.85.133.77
Ultrasonic was reported to accelerate the tosylation reaction
---Thus, you may use triethylamine (as your base) , dichloromethane (as your solvent).and p-toluene sulphonyl chloride (as your reagent) then irradiate the mixture under ultrasound for 30 min. Please see:
Pierre-Edouard Danjou, Damien Wallyn, Francine Cazier-Dennin, François Delattre, Ultrasonics Sonochemistry, Volume 19, Issue 6, November 2012, Pages 1201-1204
---You may also try pot. carbonate in ethanol and ultrasonic. Please see:
Davood Habibi, Mahmoud Nasrollahzadeh, Hesam Sahebekhtiari, Richard Vernon Parish, Tetrahedron, Volume 69, Issue 14, 8 April 2013, Pages 3082-3087
Good luck
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