Triphenylphosphine → HCID 22010521, compound

Temperature

0 °C

Diisopropyl azodicarboxylate (2.6 g) is added portionwise to a stirred solution of triphenylphosphine (3.4 g) in dry tetrahydrofuran (40 mL) at 0° C. under nitrogen. The reaction mixture is stirred at 0° C. for 15 minutes then treated with a solution of 2-fluoro-4-hydroxybenzonitrile (0.87 g) and t-butyl 3-(3-hydroxymethylphenyl)propionate (1.5 g) in dry tetrahydrofuran (10 mL) whilst maintaining the temperature at 0-5° C. Stirring is continued at this temperature for 1 hour when the reaction mixture is allowed to warm up to room temperature. The reaction mixture is evaporated to low bulk and partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase is washed with water (50 mL), dried over magnesium sulphate and evaporated. The residue is purified by flash chromatography on silica eluting with a mixture of cyclohexane and ethyl acetate (4:1 v/v). Fractions homogeneous in the required product are combined and evaporated to give tert-butyl 3-[3-(4-cyano-3-fluoro-phenoxymethyl)phenyl]propionate (0.3 g).

1. temperaturewhilst maintaining the temperature at 0-5° C
2. stirringStirring
3. waitis continued at this temperature for 1 hour
4. temperatureto warm up to room temperature
5. customThe reaction mixture is evaporated to low bulk
6. custompartitioned between ethyl acetate (100 mL) and water (100 mL)
7. washThe organic phase is washed with water (50 mL)
8. dry with materialdried over magnesium sulphate
9. customevaporated
10. customThe residue is purified by flash chromatography on silica eluting with a mixture of cyclohexane and ethyl acetate (4:1 v/v)
11. customevaporated

ORD record

ord-b17fb1428906487687abb46ac1798e6f

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06211234B1