تفاعل #1985939

معادلة التفاعل

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

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONis added
2. 2
   أخرىThe cold bath is removed
3. 3
   workup.ADDITIONdiluted with ether
4. 4
   غسيلThe ether solution is washed with 0.1M HCl, brine
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىThe residue is purified by flash chromatography
9. 9
   غسيلeluting with 10% ether in hexanes

الإجراء التجريبي

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.

المصدر