Trityl chloride → [1-(triphenylmethyl)-1H-imidazol-4-yl]methanol

Participants

Reaction Steps

4-Hydroxymethylimidazole hydrochloride (compound xiii where R2 is H) (2.50 g, 18.6 mmol) and Et3N (2.59 ml, 18.6 mmol) were combined in DMF (30 ml) and stirred at room temperature. A solution of chlorotriphenylmethane (5.19 g, 18.6 mmol) in DMF (25 ml) was added dropwise at room temperature and the resulting mixture was stirred at room temperature for about 23 hours and then poured into ice water (300 ml). The product was filtered off, washed with cold water (75 ml) and triturated with p-dioxane (30 ml). The product was filtered off and dried under reduced pressure to yield product (4.96 g, 78%). NMR (300 MHZ, DMSO-d6, 30° C.) 7.3–7.5 (9H, m), 7.25–7.35 (1H, d), 7.0–7.2 (6H, m), 6.7–6.75 (1H, s), 4.15–4.2 (2H, m).

Provenance & Evidence