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. 2020 Jun 15;26(38):8363–8367. doi: 10.1002/chem.202001598

Table 1.

Propargylation of thioacetic acid to obtain thioester 5 in flow.[a]

graphic file with name CHEM-26-8363-g009.jpg

Entry

Solvent

Base

[wt %]

Residence t

[min]

Yield 5

[%]

1

THF/CH2Cl2 (1:1)

7

20

19

2

THF/CH2Cl2 (1:1)

7

40

42

3

THF/CH2Cl2 (1:1)

7

60

45

4

THF/CH2Cl2 (1:1)

14

30

49

5

THF/CH2Cl2 (1:1)

21

30

46

6

THF

7

20

50

7

THF

21

30

79

8

THF

42

18

84

9

THF

56

14

57

10

THF

42[b]

24

82

[a] Conditions: HPLC K120 Knauer Analytical pump with thioacetic acid and propargyl bromide (0.4 m) in dry solvent, column: K2CO3/sand (20 g total) in OmniSep® column (15×150 mm). [b] Column: repacked Biotage® SNAP Ultra cartridge (30 g total). The column volume and, therefore, flow rate was varied between each run due to the percentage of base.