Ethylene Glycol → Methyl 5-(2-methyl-1,3-dioxolan-2-yl)pentanoate

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 6-oxo-heptanoic acid methyl ester (7.96 g, 50.32 mmol) in ethylene glycol (55.0 mL) was treated with trimethylorthoformate (10.65 mL, 110.14 mmol) followed by LiBF4 (963 mg, 10.06 mmol). The reaction mixture was heated at 95° C. for 14 h. The reaction mixture was cooled to rt and partitioned between EA and sat. aq. NaHCO3 The layers were separated and the aq. layer extracted with EA. The combined org. extracts were washed with sat. aq. NaHCO3, dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (50:1→2:1 hept-EA) gave the title compound as a dark yellow oil. TLC: rf (3:1 hept-EA)=0.30.

Provenance & Evidence