Hydrochloric Acid → HCID 86678085, compound

Participants

Reaction Steps

A solution of (11Z,14Z)-methyl 3-((tert-butyldimethylsilyl)oxy)icosa-11,14-dienoate (4) (5.0 g, 11.0 mmol) in CH2Cl2 (75 mL) was cooled (−78° C.) and treated, dropwise, with DIBAL (11.0 mL, 11.0 mmol; as a 1M solution in hexanes). The mixture was then warmed (−20° C.-−30° C.) and stirred (60 min). The mixture was poured into cold HCl (5% aq.), extracted with CH2Cl2, washed with brine, dried (Na2SO4), filtered and concentrated. The crude product was subjected to chromatography (1%→10% EtOAc-hexanes) to yield (11Z,14Z)-3-((tert-butyldimethylsilyl)oxy)icosa-11,14-dienal (5) (3.7 g, 79%) as a pale yellow oil. Rf 0.64 (10% EtOAc-hexanes), FW 422.79, C26H50O2Si.

Provenance & Evidence