Reacción #1985939

Ecuación de reacción

sodium hydride

methyl 2-tert-butyldimethylsilyloxymethyl-4-hydroxy-5-iodohydrocinnamate

iodomethane

1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

→

desired product

Methyl 2-Tert-butyldimethylsilyloxymethyl-4-methoxy-5-iodohydrocinnamate

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONis added
2. 2
   OtroThe cold bath is removed
3. 3
   workup.ADDITIONdiluted with ether
4. 4
   LavadoThe ether solution is washed with 0.1M HCl, brine
5. 5
   Secadodried over magnesium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroThe residue is purified by flash chromatography
9. 9
   Lavadoeluting with 10% ether in hexanes

Procedimiento

A suspension of 60% sodium hydride in mineral (1.2 g) in THF (56 ml) is cooled to -20° C. and of solution of methyl 2-tert-butyldimethylsilyloxymethyl-4-hydroxy-5-iodohydrocinnamate (12.6 g), iodomethane (5 ml) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) (8 ml) in THF (20 ml) is added. The cold bath is removed, the mixture stirred for about 2 hours, and diluted with ether. The ether solution is washed with 0.1M HCl, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography, eluting with 10% ether in hexanes, to give the desired product.

Fuente