Potassium Carbonate → HCID 45079102, compound

Participants

Reaction Steps

To a solution of (3R,6R)-3-acetoxy-6-hydroxy-7-p-toluene sulfonyloxy-hept-1-yne 31 (0.6 g, 1.76 mmol) in MeOH (10 mL) at room temperature, K2CO3 (0.536 g, 3.88 mmol) was added and the mixture was stirred for 2h. It was treated with NH4Cl solution, evaporated MeOH and the residue extracted with EtOAc (3×mL). Organic layer was washed with water (10 mL), brine (10 mL), dried (Na2SO4) evaporated. The residue obtained was purified by column chromatography (Si-gel, 20% EtOAc-hexane) to furnish (2R,5R)-5-ethynyl-2-(hydroxymethyl)-tetrahydrofuran 32 (0.22 g) in 99% yield as a colorless liquid. [α]D +20.0 (c 1.0, CHCl3); 1HNMR (CDCl3, 200 MHz): δ 1.89-2.38 (m, 4H, H-3,4), 2.4 (br.s, 1H, OH), 2.46 (d, 1H, J 2.2 Hz, H-7), 3.55 (dd, 1H, J 4.5, 11.25 Hz, H-1), 3.72 (dd, 1H, J 4.0, 11.25 Hz, H-1a), 4.0-4.15 (m, 1H, H-2), 4.52-4.66 (m, 1H, H-5); 13CNMR (CDCl3, 50 MHz): δ 26.6, 29.6, 33.6, 64.6, 68.3, 73.0, 80.7; EIMS m/z (relative intensity): 125 (M+-1, 8), 95 (74.6), 67 (100), 53 (40), 41 (80); HRMS: Calculated for C7H9O2 (M-1): 125.060255; Observed: 125.060322.

Provenance & Evidence