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. 2020 Oct 15;25(1):148–156. doi: 10.1021/acs.oprd.0c00361

Table 2. Schmidt Rearrangement in Continuous-Flowa.

graphic file with name op0c00361_0008.jpg

        yield (%)
 
entry c2a (M) acid, wt % tR (min) 3a 4a 3a:4a
1 0.20 MsOH, 67 6.7 8 10 0.8:1
2 0.20 H2SO4, 66 6.7 16 17 1:1.1
3 0.20 H2SO4, 48 8.6 14 12 1.2:1
4 0.20 H2SO4, 59 8.6 28 26 1.1:1
5 0.20 H2SO4, 69 8.6 29 26 1.1:1
6 0.20 H2SO4, 77 8.6 40 39 1:1
7 0.31 H2SO4, 77 8.6 41 37 1.1:1
a

TBAA = tetrabutylammonium azide (1.35 equiv). c2a = concentration of 2a. tR = average retention time.