Hydrochloric Acid → HCID 68495141, compound

Participants

Reaction Steps

Add diisopropylamine (11.0 mL, 78.3 mmol) to a rapidly stirred solution of 5-methoxy-2-trimethylsilanylethynyl-phenol (11.5 g, 52.2 mmol) in CH2Cl2 at room temperature under N2. Add 2-(trimethylsilyl)ethoxymethyl chloride (13.9 mL, 78.3 mmol) dropwise over 5 minutes and stir at room temperature under N2 overnight Acidify with aqueous 1N HCl solution, add water, separate layers. Extract from aqueous layer with CH2Cl2 (×2), dry combined organic layers over MgSO4 and concentrate. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-5% EtOAc/hexanes to afford 4-methoxy-2-(2-trimethylsilanyl-ethoxymethoxy)-1-trimethylsilanylethynyl-benzene (13.5 g, 74%). MS (IS) 351 (M+1)+.

Provenance & Evidence