Formaldehyde → HCID 11064432, compound

Participants

Reaction Steps

To a solution of LDA, freshly prepared from diisopropylamine (0.42 mL, 2.97 mmol) and n-BuLi (2.97 mmol), in THF (10 mL) at -78° C. was added 2-bromoquinoline (T. Young and E. Amstutz, J. Am. Chem. Soc. 73, 4773 (1951)) (570 rag, 2.7 mmol) and stirring was continued for 1 h. This mixture was cannulated into a solution of formaldehyde in THF at -78° C., which was prepared by cracking paraformaldehyde (1.24 g, 14.8 mmol) under 140°-180° C. and releasing the gas into THF (25 mL) at -23 ° C. Stirring was continued for 6.5 h at -78° C. The reaction was quenched with water (5 mL) and extracted with EtOAc (3×25 mL). After drying (MgSO4), concentration gave a light yellow solid (660 mg) which was purified by recrystallization and chromatography (silica gel, 15% EtOAc/hexanes) to give 373 mg (58%) of the product as a white solid: mp 173°-4° C. 1H NMR (300 MHz, CDCl3) δ8.24 (s, 1H), 8.05 (d, 1 H, J=8 Hz), 7.84 (d, 1 H, J=8 Hz), 7.75 (m, 1 H), 7.59 (m, 1 H). 4.90 (d, 2 H, J=6 Hz), 2.36 (rt, 1 H, J=6 Hz). Analysis calculated for C10H8BrNO was as follows: C, 50.45; H, 3.39; N, 5.88. Found: C, 50.72; H, 3.35; N, 5.94 .

Provenance & Evidence