Triethylamine → HCID 14645565, compound

Participants

Reaction Conditions

Reaction Steps

[(6-tert-Butyldiphenylsilyloxy-2-naphthyl)methoxymethylene]adamantane 1d). Approximately 7 g of a 2:1 mixture of TiCl3 and lithium aluminum hydride (Aldrich) was cautiously added to a 250 mL dry three-neck round bottom flask containing 150 mL of dry THF maintained at 0° C. by an ice bath. The resulting black mixture was stirred at 0° C. for 10 minutes and triethylamine (3.3 mL, 24 mmol) was added. The mixture was refluxed for 1 hour and a solution of methyl tert-butyldiphenylsilylnaphthoate (1.76 g, 4 mmol) and adamantanone (600 mg, 4 mmol) in 40 mL of dry THF was added over 6 hours. Reflux was continued for an additional 4 hours and the mixture cooled to room temperature.

Provenance & Evidence