Hexane → HCID 18672296, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methylbut-1-yne (0.5 g, 0.73 mmol), in dry THF (12 mL) was added dropwise at 0° C. a solution of n-butyllithium in hexane (1.6 N solution, 4.57 mL, 0.73 mmol). After being stirred for 0.25 h at 0° C., the solution was cooled at −78° C. and transferred dropwise by cannulation into a solution of ethyl pyruvate (0.80 mL, 0.73 mmol) in dry THF (12 mL) at −78° C. The resulting solution was stirred at −78° C. for 0.5 hr and quenched by the addition of saturated aqueous NH4Cl (10 mL). The mixture was extracted twice with Et2O (100 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and filtered. The filtrate solvent was removed on a rotary evaporator to give ethyl 2-hydroxy-2,5-dimethyl-3-hexynoate as a clear oil (0.85 g, 63%). LC-MS M+H=185. 1H NMR, 400 MHz, CDCl3, 4.26-4.32 ppm (m, 2H); 3.38 ppm (s, 1H); 2.53-2.58 ppm (m, 1H); 1.63 ppm (s, 3H); 1.32 ppm (t, J=7.14 Hz, 3H); and 1.15 ppm (d, J=6.96 Hz 6H).

Provenance & Evidence