Dimethyl Sulfoxide → 3-(Pyridin-2-YL)propanal

Temperature

-70 °C

35 ml (0.41 mol) of oxalyl chloride were dissolved in 700 ml of dry DCM and cooled to −70° C. A mixture of 62 ml (0.87 mol) of DMSO and 40 ml of dry DCM was added dropwise to this solution over a period of 25 min. During this, the temperature was kept strictly below −65° C. (exothermic reaction). After stirring at −70° C. for 15 min, 50 g (0.36 mol) of freshly distilled 3-(2-pyridyl)propanol dissolved in 150 ml of dry DCM were added dropwise at below −65° C. over a period not exceeding 15 min. 218 ml (0.37 mol) of TEA were added in 40 min, and then the mixture was slowly warmed to RT. 190 ml of water were added to dissolve the salts which had formed. The phases were separated, the DCM phase was concentrated in vacuo, and the product was then purified by distillation (2 mbar, 59-70° C.).

1. additionwas added dropwise to this solution over a period of 25 min
2. customwas kept strictly below −65° C.
3. custom(exothermic reaction)
4. additionwere added dropwise at below −65° C. over a period not
5. waitexceeding 15 min
6. temperaturethe mixture was slowly warmed to RT
7. dissolutionto dissolve the salts which
8. customhad formed
9. customThe phases were separated
10. concentrationthe DCM phase was concentrated in vacuo
11. distillationthe product was then purified by distillation (2 mbar, 59-70° C.)

ORD record

ord-25978dd2ca454f128592bef77c0a137d

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124587B2