反応 #1985939

反応方程式

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

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.ADDITIONis added
2. 2
   その他The cold bath is removed
3. 3
   workup.ADDITIONdiluted with ether
4. 4
   洗浄The ether solution is washed with 0.1M HCl, brine
5. 5
   乾燥dried over magnesium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The residue is purified by flash chromatography
9. 9
   洗浄eluting with 10% ether in hexanes

実験手順

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.

出典