Hydrochloric Acid → HCID 18959428, compound

Participants

Reaction Conditions

Reaction Steps

A 500 ml flask equipped with a magnetic stirring bar and a pressure equalizing addition funnel, maintained under static argon atmosphere, was charged with silane (J) (45 g, 157 mmol) dissolved in diethyl ether (100 ml). To this vigorously stirred mixture, maintained at -10° C. in an ice-acetone bath, n-butyllithium (2.5M solution in hexane, 75 ml, 188 mmol) was added dropwise over a period of 20 min. Then the mixture was allowed to warm to room temperature. The reaction was complete in 3 h (TLC, ligroin 950:EtOAc=5:1). The mixture was poured into 250 ml of cold water and acidified with hydrochloric acid. The organic layer was separated and the aqueous layer extracted with 3×75 ml portions of ether. The combined extracts were dried over magnesium sulfate, and solvents removed on a rotary evaporator to yield an orange oil, which on purification by flash chromatography (ligroin 950:Et2O=7:1) furnished 3-triethylsilylphenol (K) (23.7 g, 73% yield) as a pale yellow liquid.

Provenance & Evidence