반응 #1985939

반응 방정식

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

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONis added
2. 2
   기타The cold bath is removed
3. 3
   workup.ADDITIONdiluted with ether
4. 4
   세척The ether solution is washed with 0.1M HCl, brine
5. 5
   건조dried over magnesium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타The residue is purified by flash chromatography
9. 9
   세척eluting with 10% ether in hexanes

실험 절차

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.

출처