反应详情

To a stirred solution of 1-benzyloxy-3-chloromethyl-7-fluoro-2-methyl-naphthalene (18.5 g, 58.9 mmol) in a THF-methanol mixture (2:3; 500 mL) was added K2CO3 (8.94 g, 64.7 mmol) and PdCl2(PPh3)2 (2.06 g, 2.96 mmol) at room temperature. The solution was degassed by purging with argon for 5 minutes. The reaction mixture was stirred under a balloon of carbon monoxide overnight at room temperature. After this time, the reaction progress was monitored by TLC (5% ethyl acetate in hexanes). The reaction mixture was concentrated, and the obtained crude residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give a crude product. Silica gel chromatography (100-200 mesh, 5% ethyl acetate-hexanes) yielded (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (5.5 g, 28%) as a pale yellow solid. MS calcd. for C21H20FO3 [(M+H)+] 339, obsd. 339.0.

1. customThe solution was degassed
2. customby purging with argon for 5 minutes
3. concentrationThe reaction mixture was concentrated
4. customthe obtained crude residue
5. extractionextracted with ethyl acetate
6. washThe combined organic extracts were washed with water and brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a crude product