反应详情

A solution of CH3PPh3Br (10.72 g, 30 mmol) in anhydrous DMF (50 mL) under argon atmosphere was cooled to 0-5° C. Sodium hydride (2.0 g, 60% suspension in mineral oil, 50 mmol, 1.66 eq.) was added in portions. The mixture was stirred at room temperature for 1 hour and then 3,4-di-(methoxymethoxy)-benzaldehyde (6 g, 26.52 mmol) was added in portions. The resulting mixture was stirred at room temperature until completion of the reaction (about 2 hours). The mixture was cooled again to 0-5° C. and water (5 mL) was slowly injected to decompose the excess NaH. After an additional 10 min, the mixture was mixed with water (200 mL) and extracted with CH2Cl2 (2×200 mL). The organic layer was washed with water (200 mL), dried over anhydrous sodium sulfate, filtered and evaporated. The residue was mixed with hexanes and loaded to a silica gel column that was eluted with a mixed solvent of hexane and EtOAc to afford, after evaporation, 3.974 g of 3,4-di(methoxymethoxy)styrene as a yellowish oil (17.72 mmol, yield 66.8%). MS (ESI) m/z: 225 (M+1)+ and 247 (M+23)+.

1. stirringThe resulting mixture was stirred at room temperature until completion of the reaction (about 2 hours)
2. temperatureThe mixture was cooled again to 0-5° C.
3. waitAfter an additional 10 min
4. extractionextracted with CH2Cl2 (2×200 mL)
5. washThe organic layer was washed with water (200 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. customevaporated
9. additionThe residue was mixed with hexanes
10. washwas eluted with a mixed solvent of hexane and EtOAc
11. customto afford