Dimethylformamide → HCID 18621182, compound

Temperature

-20 °C

To a stirred solution of 1-[2-(trimethylsilanyl)ethoxy]methyl-1 H-1,2,3-triazole (Holzer, W.; Ruso, K, J. Heterocycl. Chem., 1992, 29, 1203-7) (2.0344 g, 10.2 mmol) in anhydrous THF (30 ml), cooled to <−75° C. under nitrogen, was added dropwise, over 11 min, a 1.6 M solution of butyllithium in hexanes (6.70 ml, 10.7 mmol). The mixture was stirred at this temperature for 30 min, then allowed to warm to −20° C. over 13 min. The mixture was then recooled to <−75° C., and anhydrous DMF (0.87 ml, 11.3 mmol) was added dropwise over 8 min. The mixture was stirred at <−75° C. for 1.75 h, then at 0° C. for 75 min. Saturated aqueous NH4CI (50 ml) was then added and the mixture was extracted with diethyl ether (75 ml) then ethyl acetate (2×75 ml). The organic extracts were dried (Na2SO4) and evaporated int vacuo. The residue was purified by flash chromatography (silica gel, 40% EtOAc/hexane) to give 1.7256 g (74%) of the title compound as a colourless oil: 1H NMR (360 MHz, CDCl3) δ−0.03 (9 H, s), 0.91 (2 H, m), 3.63 (2 H, m), 6.01 (2 , s), 8.28 (1 H, s), 10.08 (1 H, s); MS (ES+) m/e 170 [M—SiMe2+H]+.

1. additionwas added dropwise, over 11 min
2. customwas then recooled to <−75° C.
3. stirringThe mixture was stirred at <−75° C. for 1.75 h
4. waitat 0° C. for 75 min
5. extractionthe mixture was extracted with diethyl ether (75 ml)
6. dry with materialThe organic extracts were dried (Na2SO4)
7. customevaporated int vacuo
8. customThe residue was purified by flash chromatography (silica gel, 40% EtOAc/hexane)

ORD record

ord-38a7cd2d66e04f9c84587bd485f8a657

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06255305B1