Reacción #833560

ord-5a2150a398f34f779429e111ac0ebfed

Ecuación de reacción

O=S([O-])([O-])=S.[Na+].[Na+]
sodium thiosulphate
CC#CCBr
1-bromo-2-butyne
COC(=O)c1nc(Br)[nH]c1C(=O)OC
dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC#CCn1c(Br)nc(C(=O)OC)c1C(=O)OC
dimethyl 2-bromo-1-(but-2-ynyl)-1H-imidazole-4,5-dicarboxylate

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe organic phase is separated off
  2. 2
    Extracciónthe aqueous phase is extracted three times with ethyl acetate
  3. 3
    SecadoThe combined organic phases are dried over sodium sulphate
  4. 4
    Otrothe solvent is removed
  5. 5
    Otrothe residue is chromatographed over silica gel (cyclohexane/ethyl acetate 4:1>1:1)

Procedimiento

3.06 g 1-bromo-2-butyne are added dropwise to a mixture of 6.00 g of dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate and 3.80 g of potassium carbonate in 40 ml of dimethylformamide. The mixture is stirred for 12 h at ambient temperature and then added to an aqueous saturated solution of sodium thiosulphate. The organic phase is separated off and the aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulphate, the solvent is removed and the residue is chromatographed over silica gel (cyclohexane/ethyl acetate 4:1>1:1).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07393847B2uspto-grants-2008_07