Skip to main content
. Author manuscript; available in PMC: 2020 Mar 15.
Published in final edited form as: J Org Chem. 2019 Feb 27;84(6):3249–3259. doi: 10.1021/acs.joc.8b03162

Table 1. Reaction optimization.a.

graphic file with name nihms-1020195-t0008.jpg

Entry Solvent HCl source Conc. Conv./%a
1 DCE HCl•DMPU 1.0 64
2 CH3CN HCl•DMPU 1.0 22
3 CH3NO3 HCl•DMPU 1.0 30
4 EtOAc HCl•DMPU 1.0 90
5 DMSO HCl•DMPU 1.0 18
6 EtOAc HCl•DMPU 0.5 89
7 EtOAc HClDMPU 0.2 99
8 EtOAc HCl, Et2O 0.2 32 (98)b
9 EtOAc HCl, 2-propanol 0.2 99c
10 EtOAc HCl, dioxane 0.2 65 (94)b
11 EtOAc HCl, AcOH 0.2 99c
12 EtOAc HCl, H2O 0.2 29 (65)b
13 EtOAc CH3COCl/EtOH 0.2 99
14 EtOAc TMSCl/MeOH 0.2 95
a

Determined by GC-MS with dodecane as the internal standard.

b

24 h

c

combined with thiolated side product.