Reaktion #4355

Reaktionsgleichung

vinyl magnesium bromide

Boc-leucinal

→

desired product

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

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture was quenched with 1.0M NH4Cl (50 ml)
2. 2
   SonstigeMost of the THF was evaporated in vacuo
3. 3
   Extraktionthe residue was extracted with ether several times
4. 4
   WaschenThe combined extracts were washed (brine)
5. 5
   Trocknendried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated

Vorschrift

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.

Quelle