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 3 h. 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,55)-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): δ1.9-2.38 (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): δ26.6, 29.64, 64.62, 68.33, 73.11, 80.7, 83.92.

Provenance & Evidence