Imidazole → HCID 22125144, compound

Participants

Reaction Steps

A solution of 5 g (33 mmol) of 3-nitrobenzyl alcohol in 100 ml of dimethylformamide was treated with 10.8 g (40 mmol) of tert-butyldiphenylchlorosilane, 6.7 g (99 mmol) of imidazole and 100 mg (0.9 mmol) of 4-(dimethylamino)pyridine and the mixture stirred at ambient temperature for 4 hours. The solvent was evaporated and the residue partitioned between 100 ml of ethyl acetate and 100 ml of 2M aqueous hydrochloric acid. The organic phase was washed with a further 50 ml of 2M aqueous hydrochloric acid, dried over magnesium sulfate, filtered and evaporated to afford 12.9 g (100%) of 3-(tert-butyldiphenylsilyloxymethyl)nitrobenzene as a colorless oil. [Mass spectrum (ESI) MH+ =392].

Provenance & Evidence