Toluene → Pentadecane-7,9-diol

Participants

Reaction Conditions

Reaction Steps

A solution of 1M DIBAL-H in toluene (125.0 mL, 125 mmol) was slowly added over a period of 10 mins, to a solution of diethylmalonate (10.0 mL, 62.5 mmol, (4)) in Et2O (13.6 mL) at −78° C. under N2. The internal temperature was maintained −78° C. The mixture was stirred for 1 h at −78° C. A solution of hexylmagnesium bromide in Et2O (65.0 mL, 130 mmol) was added at −78° C. The reaction mixture was then warmed to room temperature and stirred for 6 h. The mixture was quenched with saturated NH4Cl solution at 0° C. A saturated solution of Rochelle's salt was added at room temperature and the two-phase mixture was stirred for approximately 8 h. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4. The solvent was removed in vacuum, and the resulting material was purified via column chromatography (30% Ethyacetate-70% hexanes) to provide the desired product (6.4 g, 42%, (10)).

Provenance & Evidence