Dimethyl Sulfoxide → HCID 21278431, compound

Temperature

-60 °C

18 ml of a molar solution of dimethylsulfoxide in methylene chloride were introduced dropwise at -60° C. into 9.5 ml of a molar solution of oxalyl chloride in methylene chloride and the mixture was stirred at -60° C. for 5 minutes. Then, at -60° C., a solution of 724 g of 4-hydroxy-methyl-1-(2-propynyl)-1H-pyrrole-3-carbonitrile was added dropwise and the mixture was stirred at -60° C. for 5 hours, after which, still at -60° C., 25 ml of a molar solution of triethylamine in methylene chloride were added dropwise. The mixture was stirred at -60° C. for 30 minutes and the reaction mixture was allowed to return to ambient temperature. Water was added and the mixture was stirred and decanted. The organic phase was washed with a saturated aqueous solution of sodium chloride and concentrated to dryness by distilling under reduced pressure. The residue was chromatographed over silica and was eluted with a mixture of hexane and ethyl acetate (1-1) to obtain 702 mg of 4-formyl-1-(2-propynyl)-1H-pyrrol-3-carbonitrile melting at 114° C.

1. stirringthe mixture was stirred at -60° C. for 5 hours
2. stirringThe mixture was stirred at -60° C. for 30 minutes
3. customto return to ambient temperature
4. stirringthe mixture was stirred
5. customdecanted
6. washThe organic phase was washed with a saturated aqueous solution of sodium chloride
7. concentrationconcentrated to dryness
8. distillationby distilling under reduced pressure
9. customThe residue was chromatographed over silica
10. washwas eluted with a mixture of hexane and ethyl acetate (1-1)

ORD record

ord-dd03fa13673d4c079f46debcab1a21bc

Source dataset

uspto-grants-1989_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04798901