Tetrahydrofuran → HCID 178436438, compound

Participants

Reaction Steps

In a 100 mL flame-dried three-necked flask, fitted with refluxing condenser and dropping funnel, magnesium (92 mg, 3.82 mmol), iodine (1 mg) and dry THF (6 mL) were placed under nitrogen. A light brown solution formed, the mixture was heated to reflux, and a solution of 3-bromophenoxydimethylsilane (0.899 g, 3.47 mmol) in THF (20 mL) was added by dropping funnel over 2 hr. The reaction mixture was refluxed overnight and cooled to room temperature. Ethyldimethylchlorosilane (0.681 g, 0.78 mL, 5.55 mmol) was then added by syringe. The reaction mixture was brought to reflux again for 6 hr, and allowed to stir overnight at room temperature. The reaction was then quenched with 1N HCl, and the reaction concentrated in vacuo. Extraction with CH2Cl2, aqueous workup, and column chromatography (n-hexane/ethyl acetate 8:1) yielded 3-ethyldimethylsilyl phenol (0.130 g, 0.73 mmol, 21%) as a colorless oil.

Provenance & Evidence