Table 1.
Solvent | Temp. (°C) | 20a (%) | 21 (%) | 22 (%) |
pentane | rt | 26 | 19 | 55 |
cyclohexane | 60 | 2 | 14 | 79 |
cyclohexane | 81 | 0 | 15 | 85 |
toluene | 111 | 10 | 7 | 83 |
xylenes | 140 | 13 | 4 | 83 |
aOne equivalent of DIBAL (1.0 M in cyclohexane) added to preheated solution of 20a (ca. 0.25 mmol, in 4 mL), stirred rapidly for 1 h, quenched with 20% aq w/v NaOH, extracted in EtOAc, washed with H2O and brine, dried (MgSO4) and evaporated. Yields of 21 and 22 estimated from 1H NMR analysis of the crude mixture.