Table 2. Schmidt Rearrangement in Continuous-Flowa.
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 |
TBAA = tetrabutylammonium azide (1.35 equiv). c2a = concentration of 2a. tR = average retention time.