Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 3-(2-hydroxy-ethyl)-benzonitrile (1 g; 6.79 mmol) in toluene (20 mL), was added tetrabutylammonium hydrogen sulfate (230.70 mg; 0.68 mmol; 0.10 eq.) and NaOH (20 mL; 5 M; 10 mmol) followed by the addition of tert-butyl bromoacetate (2 mL; 13.59 mmol). Reaction mixture was stirred at RT under vigorous stirring for 9 h. After this time, the aqueous phase was removed and the organic phase was diluted with EtOAc (50 mL), washed with water (50 mL) and brine (50 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give the title compound as a yellow powder (1.42 g; 80%). 1H NMR (DMSO-d6, 300 MHz) δ 7.74-7.73 (m, 1H), 7.68-7.65 (m, 1H), 7.63-7.59 (m, 1H), 7.51-7.46 (m, 1H), 3.97 (s, 2H), 3.69 (t, J=6.5 Hz, 2H), 2.88 (t, J=6.5 Hz, 2H), 1.40 (s, 9H). LC/MS (Method B): 262.1 (M+H)+.
Reaction mixture
under vigorous stirring for 9 h
After this time, the aqueous phase was removed
the organic phase was diluted with EtOAc (50 mL)
washed with water (50 mL) and brine (50 mL)
The combined organic layers were dried over magnesium sulfate
filtered
concentrated
Source ID: ord-4bb39a8cfcfa4488a1b80f860504fed6