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. 2016 May 16;7(8):5530–5536. doi: 10.1039/c6sc00932h

Table 2. Rearrangement of 8a to 6a: selected optimization.

Inline graphic
Entry Conditions a Conversion b Yield c
1 5 equiv. 16, MeOH, 170 °C, 8 h d 46% 13%
2 5 equiv. 16, MeOH, 120 °C (mW), 12 h N.D. 21%
3 0.4 equiv. 16, MeOH, 120 °C (mW), 8 h N.D. 32% e
4 0.4 equiv. 16, HFIP, 150 °C (mW), 3 h 45% 47% e , f
5 0.4 equiv. 16, HFIP, 150 °C (mW), 3 h 58% 56% e , f , g

a[8a] = 0.1 M (0.075 mmol).

bConversion was calculated based on the recovery of 8a.

cIsolated yield after column chromatography.

dThe reaction was carried out in a sealed tube.

eThe reaction vial was pretreated by N,O-bis(trimethylsilyl)acetamide.

f[8a] = 0.5 M (1 mmol).

gThe heating sequence was composed of 12 cycles with each cycle including irradiation at 150 °C for 15 min and at 50 °C for 15 min.