反应详情

温度

-70 °C

To a solution of 91.4 g of oxalyl chloride in 1.12 1 of methylene chloride, pre-cooled to -70° C., a solution of 123.4 g of dimethylsulfoxide in 0.18 l of methylene chloride was added within 25 minutes. The solution was stirred for 10 minutes at -70° C. Then, a solution of 143.3 g of 3-trityloxy-1-propanol in 0.6 l of methylene chloride was added within 25 minutes, the temperature being maintained at -65° to -70° C. Stirring was continued for another 10 minutes, and then, 182 g of triethylamine were added within 5 minutes at -65° to -70° C. The mixture was stirred for 20 minutes at -70° C. and then allowed to warm up to 10° C. within 1 hour. After the addition of 1.2 1 of water, stirring was continued for 5 minutes. The layers were separated, and the aqueous phase was extracted with 1.2 l of methylene chloride. The organic phases were washed with 1.2 l of water, dried over sodium sulfate, and the solvent was evaporated in vacuo. The residue was crystallized from ethyl acetate/hexane to yield 116.0 g of 3-trityloxypropionaldehyde as white crystals of m.p. 97°-98° C.

1. temperaturethe temperature being maintained at -65° to -70° C
2. stirringStirring
3. waitwas continued for another 10 minutes
4. stirringThe mixture was stirred for 20 minutes at -70° C.
5. temperatureto warm up to 10° C. within 1 hour
6. stirringstirring
7. waitwas continued for 5 minutes
8. customThe layers were separated
9. extractionthe aqueous phase was extracted with 1.2 l of methylene chloride
10. washThe organic phases were washed with 1.2 l of water
11. dry with materialdried over sodium sulfate
12. customthe solvent was evaporated in vacuo
13. customThe residue was crystallized from ethyl acetate/hexane