Hexane → HCID 18672296, compound

Temperature

0 °C

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).

1. temperaturethe solution was cooled at −78° C.
2. stirringThe resulting solution was stirred at −78° C. for 0.5 hr
3. customquenched by the addition of saturated aqueous NH4Cl (10 mL)
4. extractionThe mixture was extracted twice with Et2O (100 mL)
5. washThe combined organic layers were washed with brine
6. dry with materialdried over anhydrous MgSO4
7. filtrationfiltered
8. customThe filtrate solvent was removed on a rotary evaporator

ORD record

ord-f03b0413bb03471889410c1de6823145

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06515011B2