Реакция #4355

Уравнение реакции

vinyl magnesium bromide

Boc-leucinal

→

desired product

4-t-Butyloxycarbonylamino-3-hydroxy-6-methylhept-1-ene

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Другоеthe mixture was quenched with 1.0M NH4Cl (50 ml)
2. 2
   ДругоеMost of the THF was evaporated in vacuo
3. 3
   Экстракцияthe residue was extracted with ether several times
4. 4
   ПромывкаThe combined extracts were washed (brine)
5. 5
   Сушкаdried (Na2SO4)
6. 6
   Фильтрацияfiltered
7. 7
   Другоеevaporated

Методика

To a stirred 0° C. solution of Boc-leucinal (3.00 g, 13.9 mmol) in dry 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 hydroxydiastereomers in 65% field.

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