Skip to main content
. Author manuscript; available in PMC: 2011 Apr 1.
Published in final edited form as: Synlett. 2010 Oct;2010(16):2397–2402. doi: 10.1055/s-0030-1258544

Table 1. Synthesis of α-Allyl Imidates.

graphic file with name nihms241178u1.jpg

Entry Alcohol Temp/Time Imidate Yield [%]a
1 MeOH 75 °C/2 d graphic file with name nihms241178t1.jpg 4a: R = Me [81%]
2 EtOH 75 °C/2 d 4b: R = Et [43%]
3 i-PrOH 90 °C/5 d 4c: R = i-Pr [39%]
4 c-pentanol 110 °C/5 d 4d: R = c-pent [45%]
5 EtOH 85 °C/3 d graphic file with name nihms241178t2.jpg 4e: R = Et [76%]
6 i-PrOH 90 °C/4 d 4f: R = i-Pr [76%]
7 c-pentanol 115 °C/4 d 4g: R = c-pent [71%]
8 MeOH 75 °C/2 d graphic file with name nihms241178t3.jpg 4h: R = Me [95%]c
9 EtOH 75 °C/2 d 4i: R = Et [75%]
10 i-PrOH 75 °C/5 d 4j: R = i-Pr [47%]d
11 EtOH 75 °C/2 d graphic file with name nihms241178t4.jpgb 4k: R = Et [82%]
12 c-pentanol 75 °C/2 d 4l: R = c-pent [38%]
a

Isolated Yields.

b

MBS = p-methoxybenzenesulfonyl.

c

No nitrile observed in crude 1H NMR.

d

Est. nitrile yield by crude 1H NMR = 20%.