Table 1. Deprotection condition screening.
| |||
Entry | Conditions | Time/h | Conversion a /% |
1 | KI (2 equiv.) | 24 | — |
2 | KBr (2 equiv.) | 24 | — |
3 | KCl (2 equiv.) | 24 | — |
4 | KF (2 equiv.) | 24 | <1 |
5 | KI (2 equiv.), 18-C-6 (3 equiv.) | 24 | <1 |
6 | KF (2 equiv.), 18-C-6 (3 equiv.) | 24 | 1 |
7 | NaI (2 equiv.), 18-C-6 (3 equiv.) | 24 | <1 |
8 | KF (2 equiv.), 18-C-6 (3 equiv.), methyl thioglycolate (10 equiv.) | 1 | 78 |
9 | KF (2 equiv.), methyl thioglycolate (10 equiv.) | 1 | 61 |
10 | KF (1 equiv.), 18-C-6 (1 equiv.), methyl thioglycolate (2 equiv.) | 1 | 57 |
11 | Methyl thioglycolate (10 equiv.) | 24 | <1 |
12 | Methyl thioglycolate (10 equiv.). K2CO3 (2 equiv.) | 24 | 90 |
aConversion was determined by 1H NMR analysis of the reaction mixture (see ESI). All reactions were carried out in a water bath set to 50 °C.