反应详情

Add triphenylphosphine (30.3 g, 115 mmol) to crude 4-azidomethyl-2-chloro-benzoic acid methyl ester (5.8 g, 25.7 mmol) in tetrahydrofuran (152 mL) and water (4.6 mL). Stir the reaction mixture at room temperature overnight. Concentrate the reaction mixture and partition the residue between 1N hydrochloric acid and ethyl acetate. Separate the organic layer and wash the organic layer with water. Combine the aqueous layers, wash with ethyl acetate, and then neutralize with 1N sodium hydroxide. Extract the resulting aqueous mixture with ethyl acetate (3×). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate to provide the crude title compound (2.2 g, 11.0 mmol). MS (m/z): 200 (M+1).

1. concentrationConcentrate the reaction mixture
2. custompartition the residue between 1N hydrochloric acid and ethyl acetate
3. customSeparate the organic layer
4. washwash the organic layer with water
5. washwash with ethyl acetate
6. extractionExtract the resulting aqueous mixture with ethyl acetate (3×)
7. washCombine the organic layers, wash with brine
8. dry with materialdry over sodium sulfate
9. concentrationconcentrate