Trimethylsilylacetylene → 2H-Pyran-3-ol, tetrahydro-3-[2-(trimethylsilyl)ethynyl]-

Participants

Reaction Steps

A solution of dihydro-2H-pyran-3(4H)-one (200 mg, 2 mmol) in THF was treated with n-BuLi (2 mL) at −78° C. for about 30 min. Ethynyltrimethylsilane (300 mg, 3 mmol) was then added and the reaction mixture was stirred for 3 hr. Purification by gel chromatography afforded the title compound (200 mg, 50%); 1H NMR (400 MHz, DMSO) delta 0.15 (s, 9H), 1.52-1.55 (m, 1H), 1.62-1.67 (m, 1H), 1.80-1.88 (m, 1H), 3.23-3.26 (m, 1H), 3.37-3.44 (m, 1H), 3.49-3.56 (m, 2H), 5.52 (s, 1H).

Provenance & Evidence