oct-3-yn-2-ol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-hexyne (116, 2 g, 24.3 mmol) in 30 mL of freshly distilled THF at −78° C. was added n-BuLi (2.5 M solution in hexanes, 11 mL, 27 mmol) under argon (FIG. 2M). The resultant yellow solution was stirred at −78° C. for 30 min and 0° C. for 15 min. Acetaldehyde (˜2 mL) was added to this solution at −78° C. and the reaction mixture was allowed to stir at rt for 3 h. The reaction was quenched with saturated NH4Cl and extracted with Et2O (3×30 mL). The combined organic solution was washed with water, dried (MgSO4), filtered, and concentrated in vacuo. Chromatography on silica gel (EtOAc:hexanes, 1:99, then 10:90) gave 117 as a colorless oil (2.1 g, 73%). 1H NMR (CDCl3) δ4.48-4.52 (q, 1 H, J=6.0 Hz, CH), 2.17-2.22 (d of t, 2 H, J=6.7 Hz and 1.5 Hz, CH2), 1.37-1.65 (complex m, 7 H, 4 CH2 and 1 CH3), 0.88-0.93 (t, 3 H, J=7.2 Hz, CH3). to stir at rt for 3 h The reaction was quenched with saturated NH4Cl extracted with Et2O (3×30 mL) The combined organic solution was washed with water dried (MgSO4) filtered concentrated in vacuo