反应详情

To a magnetically stirred N,N-dimethylformamide (20 ml, 258.5 mmol) cooled in ice was added slowly dropwise thionyl chloride (30 ml, 411.2 mmol). To the resulting cold Vilsmeier reagent was added dichloromethane (100 ml), α-hydroxy-2-nitrobenzenepropanoic acid (20.0 g, 94.7 mmol) and a further 50 mL of dichloromethane as a rinse. The mixture, protected from extraneous moisture, was stirred at room temperature until solution was achieved and the solution was left at room temperature (25° C.) overnight. The solution was poured onto stirred ice and the mixture stirred for 1 hour during which time it warmed to room temperature. The dichloromethane layer was separated, washed thrice with water, dried (MgSO4) and evaporated to a syrup. The syrup was concentrated further at 40° C. under oil pump vacuum to remove traces of N,N-dimethylformamide. The resulting syrup was stirred magnetically with water while while cooling in ice. The resulting solid was ground in a mortar and collected on a filter. The solid was then stirred magnetically with water, collected on a filter and washed with water. Drying under vacuum over phosphorus pentoxide at room temperature provided 19.60 g (90%) of titled product, mp 107°-109° C.

1. additionThe solution was poured
2. stirringonto stirred ice
3. stirringthe mixture stirred for 1 hour during which time it
4. temperaturewarmed to room temperature
5. customThe dichloromethane layer was separated
6. washwashed thrice with water
7. dry with materialdried (MgSO4)
8. customevaporated to a syrup
9. concentrationThe syrup was concentrated further at 40° C. under oil pump vacuum
10. customto remove traces of N,N-dimethylformamide
11. stirringThe resulting syrup was stirred magnetically with water while
12. temperaturewhile cooling in ice
13. customcollected on a filter
14. stirringThe solid was then stirred magnetically with water
15. customcollected on
16. filtrationa filter
17. washwashed with water
18. dry with materialDrying under vacuum over phosphorus pentoxide at room temperature