Ethylene Glycol → HCID 7099161, compound

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 1-(5-bromo-pyridin-3-yl)-ethanone (1800 mg, 9.00 mmol) in ethylene glycol (9.57 mL, 171.69 mmol) was treated with trimethylorthoformate (2.01 mL, 18.34 mmol) followed by LiBF4 (172 mg, 1.80 mmol). The reaction mixture was heated at 95° C. overnight. Sat. aq. Na2CO3 was added and the mixture was extracted twice with ether. The combined organic extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (50:50 hept-EA)=0.57. LC-MS-conditions 02: tR=0.87 min.

Provenance & Evidence