Benzyl Chloride → HCID 70819131, compound

Participants

Reaction Conditions

Reaction Steps

Compound 5 (38 mg, 0.11 mmol) was added to a stirred suspension of oil-free NaH (5 mg, 0.11 mmol) in DMF (5 mL). When evolution of hydrogen ceased, benzyl chloride (14 mg, 0.11 mmol) was added and the mixture was heated at 50° C. for 4 h. The reaction mixture was added to water (5 mL), extracted with portions of ethyl ether. The combined organic phase was dried over anhydrous MgSO4 and concentrated under diminished pressure to afford a crude residue. Elution with 1:1 hexane/ethyl acetate gave 4-(benzyloxy)-3-heptyl-5-iodo-2,6-dimethylpyridine (19) as a light yellow oil: yield 38 mg (80%); silica gel TLC Rf 0.7 (1:1 hexane/ethyl acetate); 1H NMR (CDCl3) δ 0.61-0.89 (m, 3H), 1.26-1.31 (m, 10H), 2.504 (s, 3H), 2.62-2.65 (m, 2H) 2.75 (s, 3H), 4.95 (s, 2H), 7.38-7.43 (m, 4H) and 7.55-7.57 (m, 1H).

Provenance & Evidence