Water → HCID 67336694, compound

To a solution of 5-bromo-1-(3-(tert-butyldimethylsilyloxy)-1-phenylpropyl)-3-nitro-1H-1,2,4-triazole (510 mg, 1.16 mmol) in tetrahydrofurane (11.6 mL) was added under an atmosphere of nitrogen at room temperature 1 M tetrabutyl ammonium fluoride solution in tetrahydrofurane (3.47 mL, 3.47 mmol). The yellow solution was stirred at room temperature over night. Water was added and the aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a light yellow solid (174 mg, 61%) after column chromatography on silica gel using a gradient from heptane/ethyl acetate 4:1 to 1:1 (v/v) as eluent. MS ISP (m/e): 247.2 (100) [(M+H)+], 264.1 (36). 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.42-7.38 (m, 3H), 7.09 (d, 2H), 5.61 (t, 1H), 4.56 (m, 2H), 2.77 (m, 1H), 2.42 (m, 1H).

1. extractionthe aqueous phase was extracted twice with ethyl acetate
2. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution and brine
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. customthe solvent was evaporated under reduced pressure

ORD record

ord-6fe9f8502ffc4679bef91278a651db02

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08486967B2