Reacción #422249

ord-aab0b5a5d28b46a095e8d5f7ca003a30

Ecuación de reacción

COC(=O)CP(=O)(C(=O)c1c(C)cc(C)cc1C)C(=O)c1c(C)cc(C)cc1C
methyl 2-(bis(2,4,6-trimethylbenzoyl)-phosphinyl)acetate
C#CCO
2-propyn-1-ol
CCCCCCCCCCCC(=O)[O-].CCCCCCCCCCCC(=O)[O-].CCC[CH2][Sn+2][CH2]CCC
dibutyltin dilaurate
→
C#CCOC(=O)CP(=O)(C(=O)c1c(C)cc(C)cc1C)C(=O)c1c(C)cc(C)cc1C
propyn-3-yl 2-[bis(2,4,6-trimethylbenzoyl)-phosphoryl]acetate
Rendimiento 55.0%

Reactantes

COC(=O)CP(=O)(C(=O)c1c(C)cc(C)cc1C)C(=O)c1c(C)cc(C)cc1C
methyl 2-(bis(2,4,6-trimethylbenzoyl)-phosphinyl)acetate
C#CCO
2-propyn-1-ol
CCCCCCCCCCCC(=O)[O-].CCCCCCCCCCCC(=O)[O-].CCC[CH2][Sn+2][CH2]CCC
dibutyltin dilaurate

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.DISTILLATIONExcess 2-propyn-1-ol is distilled off under vacuum
  2. 2
    Otrothe residual oil purified by preparative column chromatography (silica gel, eluent toluene/ethyl acetate 9:1)

Procedimiento

2.9 g (7 mmol) methyl 2-(bis(2,4,6-trimethylbenzoyl)-phosphinyl)acetate (example 22) is dissolved in a tenfold excess of 2-propyn-1-ol and heated to 90° C. during 12 hours in the presence of 10 mol % dibutyltin dilaurate. Excess 2-propyn-1-ol is distilled off under vacuum and the residual oil purified by preparative column chromatography (silica gel, eluent toluene/ethyl acetate 9:1). 1.7 g (55%) propyn-3-yl 2-[bis(2,4,6-trimethylbenzoyl)-phosphoryl]acetate are obtained as yellowish oil.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08883872B2uspto-grants-2014_11