Sodium Iodide → Trans-2-(Cyanomethyl)-5-(2'-methoxy-5'-fluorophenethyl)tetrahydrofuran

Temperature

70 °C

To a vial under Ar(g) was added 2-(bromomethyl)-5-(2′-methoxy-5′-fluorophenethyl)tetrahydrofuran (0.67 g, 2.1 mmol), NaI (70 mg), potassium cyanide (0.35 g, 5.3 mmol), and dry DMSO (5 mL). The mixture thus obtained was heated to 70° C. under Ar for 12 h. After it was cooled to room temperature, the reaction mixture was poured into a separatory funnel containing sodium bicarcarbonate aqueous solution (sat. NaHCO3:H2O=1:1, 40 mL). The organic function was extracted with ethyl acetate (2×50 mL) and the combined organic layers were washed with brine (50 mL) and dried over sodium sulfate. The solvent then was removed in vacuo and crude product thus obtained was purified by flash column chromatography (15% EtOAc in hexane) to result in the title product (448 mg, 86%).

1. customThe mixture thus obtained
2. temperatureAfter it was cooled to room temperature
3. additionthe reaction mixture was poured into a separatory funnel
4. extractionThe organic function was extracted with ethyl acetate (2×50 mL)
5. washthe combined organic layers were washed with brine (50 mL)
6. dry with materialdried over sodium sulfate
7. customThe solvent then was removed in vacuo and crude product
8. customthus obtained
9. customwas purified by flash column chromatography (15% EtOAc in hexane)

ORD record

ord-d7b364658c144320a428647d402c70d9

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08168635B2