Imidazole → 4-(tert-Butyldimethylsiloxy)phenol

Participants

Reaction Steps

4-Hydroxyphenyl benzoate (9.0 mmol) was dissolved in CH2Cl2 (9 mL/mmol), TBDMS-Cl (1.5 eq., 13.5 mmol) and imidazole (2.0 eq., 18.0 mmol) were added and the mixture was stirred at r.t. overnight. The mixture was diluted with MeOH (4.5 mL/mmol), and NaBH4 (2.5 eq., 22.5 mmol) was added slowly over 5 min (attention: vigorous gas evolution). The mixture was concentrated by removing CH2Cl2 under reduced pressure and the suspension was heated to 65° C. for 15 h.

Provenance & Evidence