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0 °C

A mixture of NaH (3.2 g, 79 mmol) in 50 mL NMP stirred at 0° C., was treated dropwise with a mixture of 2-(3-methoxyphenyl)acetonitrile (3.9 g, 26 mmol) and 1-bromo-2-(2-bromoethoxy)ethane (6.1 g, 26 mmol) in 20 mL. The mixture was allowed to warm to room temperature and stirred for 15 hours, M+1=218. The mixture was then carefully quenched with 100 mL H2O and the pH was adjusted to 5. The mixture was extracted with ether (3×100 mL). The combined organic layers were washed with H2O (3×50 mL) and brine (20 mL). The organic layer was dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 10-20% EtOAc/hexane to give 5.28 g of the crude product 5.28 g as a pale yellow oil. MS (m/z)=218 (M+H)+.

1. temperatureto warm to room temperature
2. stirringstirred for 15 hours
3. customThe mixture was then carefully quenched with 100 mL H2O
4. extractionThe mixture was extracted with ether (3×100 mL)
5. washThe combined organic layers were washed with H2O (3×50 mL) and brine (20 mL)
6. dry with materialThe organic layer was dried over anhydrous Na2SO4
7. concentrationconcentrated in vacuo
8. custompurified by column chromatography
9. washeluting with 10-20% EtOAc/hexane