Potassium Carbonate → HCID 12066282, compound

Participants

Reaction Steps

A solution of (3S,6S)-3-acetoxy-6-hydroxy-7-p-toluene sulfonyloxy-hept-1-yne 15 (3.67 g, 10.79 mmol) in MeOH (50 mL) at room temperature, was treated with K2CO3 (3.2 g, 23.7 mmol) and stirred for 3h. It was further treated with NH4Cl solution, evaporated MeOH and residue extracted with EtOAc (3×50 mL). Organic layer was washed with water (2×25 mL), brine (25 mL), dried (Na2SO4), and evaporated. The residue obtained was purified by column chromatography (Si-gel, 20% EtOAc-hexane) to afford (2S,5S)-5-ethynyl-2-(hydroxymethyl)-tetrahydrofuran 16 (1.35 g) in 90% yield as a colorless liquid. [α]D −15.07 (c 1.26, CHCl3); 1HNMR (CDCl3, 200 MHz): δ 1.9-2.38 (m, 4H, H-3,4), 2.45 (d, 1H, J 2.1 Hz, H-7), 3.55 (dd, 1H, J 6.3,12.75 Hz, H-1), 3.72 (dd, 1H, J 3.8, 12.75 Hz, H-1a), 4.0-4.18 (m, 1H, H-2), 4.55-4.65 (m, 1H, H-5); 13CNMR (CDCl3, 50 MHz): δ 26.6, 29.64, 64.62, 68.33, 73.11, 80.7, 83.92.

Provenance & Evidence