tert-butyl 2-(4-Methoxybenzylidene)hydrazinecarboxylate synthesis

Yield:150767-00-3 95%

Reaction Conditions:

with pyridinium p-toluenesulfonate in dichloromethane at 20; for 0.123333 h;Flow reactor;

Steps:

General procedure for the continuous-flow hydrazone synthesis (products 3a-j)

General procedure: General procedure for the continuous-flow hydrazone synthesis (products 3a-j) Following initiation of the control script, using the apparatus shown in Figure 3, the system was primed with dichloromethane and the aqueous extraction solvent for several minutes until there were no air gaps in the flow path. The aldehyde (0.20 M) and pyridinium paratoluenesulfonate (PPTS) (0.10 M) in dichloromethane (7.5 mL) were loaded in to the corresponding 7.5 mL injection loop. tert-Butyl carbazate (0.4 M) in dichloromethane (10.0 mL) was loaded into the 10.0 mL injection loop. The tert-butyl carbazate loop was injected into the system 30 seconds prior to the substrate loop. Organic solution exiting the system was collected for 40 minutes. The solvent was then removed under reduced pressure to afford a solid.

References:

O'Brien, Matthew;Cooper, Dennis A.;Mhembere, Panashe [Tetrahedron Letters,2016,vol. 57,# 47,p. 5188 - 5191] Location in patent:supporting information