Water → 3-(1H-Imidazol-4-yl)-1-propanol

Participants

Reaction Steps

Add lithium aluminum hydride (1M in tetrahydrofuran; 17 mL; 2.0 equiv; 17.00 mmoles) dropwise over 5 minutes to a 0° C. solution of methyl 3-(1H-imidazol-4-yl)propanoate (2.2 g; 1.0 equiv; 8.52 mmoles) in tetrahydrofuran (85 mL). Warm the reaction mixture to ambient temperature and stir for 16 hours. Add water (0.65 mL), 15% sodium hydroxide (0.65 mL), and water (1.95 mL) sequentially, then stir for 30 minutes. Filter the resulting solid and rinse with acetone. Concentrate the filtrate to afford 3-(1H-imidazol-5-yl)propan-1-ol (3.0 g; 61%) as a white solid. To further purify the product, suspend a portion of 3-(1H-imidazol-4-yl)propan-1-ol (1.5 g) in water (50 mL) and stir at 100° C. for 2 hours. Filter the product mixture and concentrate the filtrate to afford pure 3-(1H-imidazol-5-yl)propan-1-ol (0.5 g) as an off white solid: MS (m/z): 127(M+1).

Provenance & Evidence