反应详情

To a solution of (S)-methyl 2-(tert-butyldimethylsilyloxy)-4-mesylbutanoate (91d, 4.9 g, 15 mmol) in anhydrous acetone was added sodium iodide (11.5 g, 75 mmol). The reaction was heated at reflux for 1.5 h. The reaction was quenched with water and extracted into EtOAc×3. The combined organic phases were washed with brine then dried over anhydrous sodium sulfate. The solvent was removed in vacuo to yield (S)-methyl 2-(tert-butyldimethylsilyloxy)-4-iodobutanoate (91e, 4.33 g, 12 mmol) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 0.07-0.13 (m, 6H), 0.82-0.99 (m, 9H), 2.09-2.32 (m, 2H), 3.17-3.36 (m, 2H), 3.74 (s, 3H), 4.29 (dd, J=8.08, 4.04 Hz, 1H).

1. temperatureThe reaction was heated
2. temperatureat reflux for 1.5 h
3. customThe reaction was quenched with water
4. extractionextracted into EtOAc×3
5. washThe combined organic phases were washed with brine
6. dry with materialthen dried over anhydrous sodium sulfate
7. customThe solvent was removed in vacuo