Bicyclo(2.2.1)heptan-2-one → 2-((Trimethylsilyl)ethynyl)bicyclo[2.2.1]heptan-2-ol

Participants

Reaction Steps

Bicyclo[2.2.1]heptan-2-one (1.1 g, 10 mmol) in THF was treated with n-BuLi (6 mL, 2.5 M in n-hexane) at −78° C. for about 30 min. Ethynyltrimethylsilane (1.1 g, 11 mmol) was then added and the reaction mixture was stirred for 3 hr. Purification by gel chromatography afforded the title compound (1.6 g); 1H NMR (400 MHz, DMSO) delta 0.16 (s, 9H), 1.15-1.44 (m, 4H), 1.64-1.67 (m, 1H), 1.88-1.93 (m, 2H), 2.07-2.22 (m, 3H), 3.94 (s, 1H).

Provenance & Evidence