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. Author manuscript; available in PMC: 2011 Feb 5.
Published in final edited form as: Org Lett. 2010 Feb 5;12(3):532–535. doi: 10.1021/ol902720d

Table 2.

Deprotection to β- and ortho-Hydroxy Ketonesa

entry starting material product yield
1 graphic file with name nihms168016t29.jpg graphic file with name nihms168016t30.jpg 80%
2 graphic file with name nihms168016t31.jpg graphic file with name nihms168016t32.jpg 56%
3 graphic file with name nihms168016t33.jpg graphic file with name nihms168016t34.jpg 83%
4 graphic file with name nihms168016t35.jpg graphic file with name nihms168016t36.jpg 89%
a

Conditions entries 1–3 (one pot): K2CO3 (3 × 0.15 equiv/2.5 h), MeOH, 25 °C, then 3.5 equiv NaHSO3, H2O, 80 °C, 3 h; Conditions entry 4 (two steps): (i) 0.15 equiv K2CO3, MeOH, 25 °C, 1 h, then (ii) 3.5 equiv NaHSO3, H2O, EtOH, 90 °C, 12 h.