Diisopropylethylamine → HCID 68851718, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4S)-3-(7-octenoyl)-4-benzyl-1,3-oxazolidin-2-one (2.24 g, 7.59 mmol) and titanium (IV) chloride (1M in dichloromethane, 8.0 mL, 7.97 mmol) in dichloromethane (35 mL) at 0° C. was added dropwise diisopropylethylamine (1.5 mL, 8.35 mmol). After stirring at 0° C. for 1 hour, the resulting titanium enolate was then reacted with a solution of trioxane (0.82 g, 9.11 mmol) in dichloromethane (7 mL), followed by the addition of a solution of titanium (IV) chloride (1M in dichloromethane, 8.0 mL, 7.97 mmol). The reaction mixture was then stirred at 0° C. for 4 h. The reaction mixture was then quenched with saturated ammonium chloride (50 mL). The aqueous layer was extracted with dichloromethane (100 mL×2). The organic extracts were washed with brine, and dried over MgSO4, filtered and concentrated in vacuo to yield the title compound. MH+332.

Provenance & Evidence