Diisobutylaluminum hydride → HCID 86605034, compound

Participants

Reaction Conditions

Reaction Steps

To 13.9 g (23 mmol) of allylic ester XIII in 500 ml of THF at −78° C. was added over 10 min 47 ml (70 mmol) of DIBALH (1.5 M in toluene). The reaction mixture was successively stirred at −78° C. for 3 h, allowed to warm to 0° C. within 30 min. and further stirred at 0° C. for 30 min. before being quenched by the addition of 50 ml of aqueous 0.1N HCl. The layers were separated and the aqueous layer was washed with TBME (2×50 ml). The combined organic extracts were washed with aqueous saturated NaHCO3 (2×50 ml) and brine (50 ml), dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash-chromatography (SiO2, 5:1 heptane/EtOAc) to afford 10.0 g (76%) of allylic alcohol XIV as a pale yellowish oil. Rf=0.16 (SiO2, 3:1 heptane-AcOEt).

Provenance & Evidence