反应详情

温度

0 °C

A cooled (0° C.) suspension of aluminum chloride (9.316 g; 69.87 mmol) in anh. DCE (50 ml) was treated with commercially available 1,3,5-trimethoxybenzene (7.664 g; 45.56 mmol), and stirring at 0° C., under nitrogen, was continued for 10 min. Commercially available methyl 5-chloro-5-oxopentanoate (5.000 g; 30.37 mmol) was then added, and the mixture was stirred at rt for 26 h. The resulting reaction mixture was poured onto crushed ice (150 g), and DCM (100 ml) was added. The separated aq. layer was further extracted with DCM (3×50 ml). The mixed organic layers were washed successively with water (75 ml) and brine (2×75 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=10/1 to AcOEt) afforded methyl 5-oxo-5-(2,4,6-trimethoxyphenyl)pentanoate as a yellow oil. LC-MS (conditions D): tR=0.94 min.; [M+H]+: 297.13 g/mol.

1. temperatureA cooled
2. stirringthe mixture was stirred at rt for 26 h
3. customThe resulting reaction mixture
4. additionwas poured
5. additionwas added
6. extractionThe separated aq. layer was further extracted with DCM (3×50 ml)
7. washThe mixed organic layers were washed successively with water (75 ml) and brine (2×75 ml)
8. dry with materialdried over anh. MgSO4
9. filtrationfiltered
10. concentrationconcentrated to dryness under reduced pressure
11. customPurification by FC (heptane/AcOEt=10/1 to AcOEt)