Reacción #1985944

ord-cf38f96581534566aa8c89c9a242ad2a

Ecuación de reacción

COC(=O)CCc1cc(OC(C)=O)c(OC)cc1C=O
methyl 5-acetoxy-2-formyl-4-methoxyhydrocinnamate
c1c[nH]cn1
imidazole
CC(C)(C)[Si](C)(C)Cl
tert-butylchlorodimethylsilane
→
COC(=O)CCc1cc(OC(C)=O)c(OC)cc1CO[Si](C)(C)C(C)(C)C
desired product
COC(=O)CCc1cc(OC(C)=O)c(OC)cc1CO[Si](C)(C)C(C)(C)C
Methyl 5-Acetoxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate

Reactantes

COC(=O)CCc1cc(OC(C)=O)c(OC)cc1C=O
methyl 5-acetoxy-2-formyl-4-methoxyhydrocinnamate
c1c[nH]cn1
imidazole
CC(C)(C)[Si](C)(C)Cl
tert-butylchlorodimethylsilane

Reactivos

Ninguno

Disolventes

CCOCC
ether
O
water
ClCCl
methylene chloride
ClCCl
methylene chloride

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadothe organic layer washed with water, brine
  2. 2
    Secadodried over magnesium sulfate
  3. 3
    Filtraciónfiltered
  4. 4
    Concentraciónconcentrated in vacuo

Procedimiento

To a solution of methyl 5-acetoxy-2-formyl-4-methoxyhydrocinnamate (3.31 g) and imidazole (2.42 g) in methylene chloride (25 ml) is added a solution of tert-butylchlorodimethylsilane (2.73 g) in methylene chloride (25 ml). The mixture is stirred at room temperature for about 60 minutes, diluted with ether and water, and the organic layer washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give the desired product.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05571506uspto-grants-1996_11