Diethyl Ether → Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

Participants

Reaction Steps

Tetrabutylammonium fluoride (1 M THF, 44 mL, 44 mmol) was added to a 0° C. solution of 1-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)benzene (14 g, 40 mmol) in THF (400 mL). The reaction was stirred for 30 minutes, then poured into a mixture of saturated NH4Cl and Et2O. The layers were separated and the aqueous phase was extracted twice with Et2O. The organics were combined, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was chromatographed (1:9 EtOAc/hexanes) to provide the product as a colorless oil (8.0 g, 85%).

Provenance & Evidence