反应详情

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)+.

1. customReaction mixture
2. stirringunder vigorous stirring for 9 h
3. customAfter this time, the aqueous phase was removed
4. additionthe organic phase was diluted with EtOAc (50 mL)
5. washwashed with water (50 mL) and brine (50 mL)
6. dry with materialThe combined organic layers were dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated