Reaktion #83150

Reaktionsgleichung

potassium carbonate

1-octene

(5R)-3-(4-bromophenyl)-5-phenyl-2-oxazolidinone

→

(5R)-3-(4-octylphenyl)-5-phenyl-2-oxazolidinone

Ausbeute 17.0%

Lösungsmittel

THF

DMF

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGfurther stirring for 2 hours at about 10° C
2. 2
   Temperaturunder cooling on an ice bath
3. 3
   workup.STIRRINGstirring for 3 hours at 63.5°-70 ° C. (inner temperature)
4. 4
   SonstigeAfter the reaction
5. 5
   Sonstigeto precipitate a crystal
6. 6
   FiltrationThe crystal was recovered by filtration
7. 7
   Waschenwashed with water
8. 8
   Sonstigefollowed by purification by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) and recrystallization from acetone

Vorschrift

0.40 g (3.56 mM) of 1-octene and 2 ml of dry tetrahydrofuran (THF) were placed in 50 ml-three necked flask. To the mixture, 7.6 ml of 0.5M-9-borabicyclo[3.3.1]-nonane-(9-BBN) in THF was gradually added dropwise on an ice-common salt bath at -15° to -13° C. (inner temperature) in nitrogen atmosphere, followed by stirring for 1 hour at the same temperature and further stirring for 2 hours at about 10° C. To the resultant mixture, a solution of 0.80 g (2.51 mM) of (5R)-3-(4-bromophenyl)-5-phenyl-2-oxazolidinone synthesized in Example 3 in 11 ml of DMF was added under cooling on an ice bath, followed by addition of 0.08 g of tetrakis (triphenylphosphine) palladium (O) and 0.70 g of potassium carbonate in succession and then stirring for 3 hours at 63.5°-70 ° C. (inner temperature). After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by purification by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) and recrystallization from acetone to obtain 0.15 g of (5R)-3-(4-octylphenyl)-5-phenyl-2-oxazolidinone (Yield: 17.0%).

Quelle