반응 #4352

반응 방정식

Boc-leucinal

vinyl magnesium bromide

→

desired product

수율 65.0%

(3RS,4S)-4-t-Butyloxycarbonylamino-3-hydroxy-6-methylhept-1-ene

수율 65.0%

용매

tetrahydrofuran

THF

반응 조건

후처리

1. 1
   기타the mixture was quenched with 1.0M NH4Cl (50 ml)
2. 2
   기타Most of the THF was evaporated in vacuo
3. 3
   추출the residue was extracted with ether several times
4. 4
   세척The combined extracts were washed (brine)
5. 5
   건조dried (Na2SO4)
6. 6
   여과filtered
7. 7
   기타evaporated

실험 절차

To a stirred 0° C. solution of Boc-leucinal (3.00 g, 13.9 mmol) in dry tetrahydrofuran (THF) (70 ml) was added vinyl magnesium bromide (35 ml of a 1.0M solution in THF). After 5 hours, the mixture was quenched with 1.0M NH4Cl (50 ml). Most of the THF was evaporated in vacuo and the residue was extracted with ether several times. The combined extracts were washed (brine), dried (Na2SO4), filtered, and evaporated to give the desired product as a 3:2 mixture of hydroxy diastereomers in 65% yield.

출처