Reaktion #4354

Reaktionsgleichung

resultant compound

(4S)-2,8-Dimethyl-4-[(toluenesulfonyl)amino]-5-nonanone

vinyl magnesium bromide

→

desired product

Ausbeute 95.0%

(4S)-2,8-Dimethyl-5-hydroxy-4-[(toluenesulfonyl)amino]-5-vinylnonane

Ausbeute 95.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched (8 ml H2O+2 ml brine)
2. 2
   Extraktionextracted with ether (3×4 ml)
3. 3
   WaschenThe combined ether phase was washed (4 ml brine)
4. 4
   Trocknendried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated

Vorschrift

To a stirred 0° C. solution of the resultant compound of Example 5 (79 mg, 0.23 mmol) in dry THF (8 ml) was added vinyl magnesium bromide (1.5 ml of a 1.0M solution in THF) dropwise. The mixture was warmed (room temperature, 10 hours), quenched (8 ml H2O+2 ml brine), acidified with 0.1M H3PO4 (pH=7), and extracted with ether (3×4 ml). The combined ether phase was washed (4 ml brine), dried (Na2SO4), filtered, and evaporated to give 81 mg (95%) of the desired product as a 4:1 mixture of diastereomers.

Quelle