Acetaldehyde → HCID 69937523, compound

Participants

Reaction Conditions

Reaction Steps

n-BuLi (1375 μl, 2.200 mmol) was added dropwise to a solution of 2,2,6,6-tetramethylpiperidine (407 μl, 2.400 mmol) in THF (5 mL) at −78° C. under inert gas (N2). The resulting mixture was stirred at ˜−50° C. for 1 hr. 5-bromonicotinic acid (202 mg, 1 mmol) in THF (5 mL) was added at this temperature. The resulting mixture was stirred for 45 min at −50° C. acetaldehyde (56.5 μl, 1.000 mmol) was added and the resulting mixture was stirred for 60 min. The reaction was quenched by NH4Cl (saturated solution) and warmed up to room temperature. After acidified to pH 2 with HCl, the resulting mixture was heated to reflux for 8 hrs. After concentration, acid-base extraction and concentration again, the residue was purified by column (Heptane/ethyl acetate v/v, 10-20%) yielded colorless solid. 1H NMR (400.3 MHz, CDCl3): δ 1.77 (d, J=6.7 Hz, 3H), 5.56 (q, J=6.7 Hz, 1H), 8.91 (s, 1H), 9.08 (s, 1H).

Provenance & Evidence