Reaction #72549

Reaction equation

MeOH

oxazolidin-2-one

NaH

1-bromomethyl-4-nitro-benzene

→

title product

3-(4-Nitro-benzyl)-oxazolidin-2-one

Solvents

water

THF

THF DMF

Conditions

Workup

1. 1
   workup.ADDITIONthere is added
2. 2
   Otheris brought to ambient temperature
3. 3
   workup.ADDITIONis added dropwise at 0° C
4. 4
   workup.STIRRINGThe reaction mixture is then stirred overnight at ambient temperature
5. 5
   OtherThe suspension obtained
6. 6
   Concentrationis then concentrated
7. 7
   workup.ADDITIONpoured into 500 ml of water
8. 8
   ExtractionThe solution is then extracted with DCM
9. 9
   OtherThe organic phase obtained
10. 10
    Washis washed with water and with saturated aqueous NaCl solution
11. 11
    Dryingis dried over sodium sulphate
12. 12
    Filtrationis then filtered
13. 13
    OtherThe filtrate obtained
14. 14
    Concentrationis concentrated
15. 15
    Otherthe solid formed
16. 16
    Filtrationis filtered off
17. 17
    Washwashed with ethyl ether
18. 18
    Otherdried in vacuo

Procedure

To a suspension of NaH (60% as a dispersion in oil, 0.34 mol) in anhydrous THF (60 ml) at 0° C. there is added, dropwise, a solution of oxazolidin-2-one (0.31 mol) under an inert atmosphere. The reaction mixture is brought to ambient temperature and stirred for one hour. A solution of 1-bromomethyl-4-nitro-benzene (0.35 mol) in a mixture of THF/DMF (10/1) (250 ml) is added dropwise at 0° C. The reaction mixture is then stirred overnight at ambient temperature. The solution is then cooled to 0° C. There are then added, in succession, 20 ml of MeOH and 20 ml of water. The suspension obtained is then concentrated and then poured into 500 ml of water. The solution is then extracted with DCM and the organic phases are combined. The organic phase obtained is washed with water and with saturated aqueous NaCl solution, is dried over sodium sulphate and is then filtered. The filtrate obtained is concentrated and the solid formed is filtered off, washed with ethyl ether and then dried in vacuo to yield the title product, which is used directly in the next Step.

Source