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. Author manuscript; available in PMC: 2015 Jun 17.
Published in final edited form as: Org Lett. 2008 Apr 26;10(11):2135–2138. doi: 10.1021/ol800532p

Table 1.

Preparation of Potassium Alkoxymethyltrifluoroboratesa

graphic file with name nihms694691u2.jpg
entry nucleophile reaction time (h) product isolated yield (%)
1 graphic file with name nihms694691t1.jpg 3 graphic file with name nihms694691t2.jpg 2a 98
2 graphic file with name nihms694691t3.jpg 5 graphic file with name nihms694691t4.jpg 2b 97
3 graphic file with name nihms694691t5.jpg 11 graphic file with name nihms694691t6.jpg 2c 91b
4 graphic file with name nihms694691t7.jpg 7 graphic file with name nihms694691t8.jpg 2d 99
5 graphic file with name nihms694691t9.jpg 5 graphic file with name nihms694691t10.jpg 2e 75
6 graphic file with name nihms694691t11.jpg 24 graphic file with name nihms694691t12.jpg 2f 95
7 graphic file with name nihms694691t13.jpg 6 graphic file with name nihms694691t14.jpg 2g 86
8 MeONa 14 graphic file with name nihms694691t15.jpg 2h 91b
9 graphic file with name nihms694691t16.jpg 3 graphic file with name nihms694691t17.jpg 2i 84
10 graphic file with name nihms694691t18.jpg 5 graphic file with name nihms694691t19.jpg 2j 98
11 graphic file with name nihms694691t20.jpg 5 graphic file with name nihms694691t21.jpg 2k 92
a

Conditions: ROH (3 equiv), NaH (3 equiv), THF (0.2 M), 0 °C–rt.

b

Commercially available alkoxide was used.