Myristyl bromide → HCID 21839216, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of di-tert butyl malonate (10.80 g, 50 mmol) and t-BuOK (5.60 g, 50 mmol) was stirred (30 min, 75° C.) in t-BuOH (150 mL, dried over 4 Å sieves). To this was added a solution of 1-bromotetradecane (13.85 g, 50 mmol) and the reaction stirred at 75° C. overnight. Solvent was removed by rotary evaporation, giving a white semi-solid, which was partitioned between CH2Cl2 (100 mL) and saturated aqueous NaCl (2×300 mL), dried (MgSO4) and evaporated to a colorless oil (15.3 g). Purification by silica gel flash chromatography (100% hexane incremented to hexane:CH2Cl2 (70:30)) gave product 34 as a colorless oil (10.0 g, 48%). High resolution FAB MS:C25H49O4 (M+H); Theor. 413.3630855. Found 413.3627625.

Provenance & Evidence