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. 2016 Aug 16;12:1851–1862. doi: 10.3762/bjoc.12.174

Table 1.

Temperature and solvent effects from the addition of DIBAL to 20a.a

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.