Boron trifluoride etherate → HCID 10685967, compound

Participants

Reaction Conditions

Reaction Steps

Butyllithium (48 ml, 1.6 M) was added to triethylsilylacetylene (10.7 g, 76.4 mmol) in THF (90 ml) at -78° C. over 20 min. After 10 min BF3.OEt2 (10 ml, 82 mmol) was added, then after another 10 min (-)-benzyl-(R)-glycidyl ether (8.4 g, 51 mmol) in THF (20 ml) was added over 10 min. The mixture was stirred at -78° C. for 1 h then at 0° C. for 20 min. Saturated NH4Cl was added and the mixture extracted with EtOAc (×3). The combined organic layers were washed with H2O and brine, dried, evaporated, and purified by chromatography to give (R)-5-benzyloxy-4-hydroxy-1-triethylsilyl-1-pentyne (9.4 g, 61%).

Provenance & Evidence