Sodium hydride → 2-(4-{2-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethyl acetate

HRID 916797Notes

Reaction equation

HRID 916797 reaction equation
[CH3:1][C:2]1([CH3:18])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@H:12]3[O:16][C:15](=[O:17])[NH:14][CH2:13]3)=[CH:11][C:5]=2[CH2:4][O:3]1.[H-].[Na+].[C:21]([O:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][CH2:35]Br)=[CH:30][CH:29]=1)(=[O:23])[CH3:22]>CN(C=O)C>[C:21]([O:24][CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][CH2:35][N:14]2[CH2:13][C@@H:12]([C:10]3[CH:9]=[CH:8][C:6]4[O:7][C:2]([CH3:18])([CH3:1])[O:3][CH2:4][C:5]=4[CH:11]=3)[O:16][C:15]2=[O:17])=[CH:32][CH:33]=1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneHCID 693900572-[4-(2-Bromoethyl)phenoxy]ethyl acetate

Product 1

HCID 693917962-(4-{2-[(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}phenoxy)ethyl acetateYield 44.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (651 mg) in DMF (15 mL) was treated with sodium hydride (84 mg) under nitrogen and stirred for 1 h. A solution of 2-[4-(2-bromoethyl)phenoxy]ethyl acetate (500 mg) in DMF (5 mL) was added and the reaction mixture was stirred for a further 2 h. This was then concentrated in vacuo and the residue was taken up in EtOAc, washed with water, brine and dried (MgSO4). The solution was concentrated in vacuo and the residue was purified by chromatography (Biotage, 90 g) eluting with cyclohexane-EtOAc (2:1) to give the title compound (355 mg). LCMS RT=3.26 min.

Workup

  1. stirringthe reaction mixture was stirred for a further 2 h
  2. concentrationThis was then concentrated in vacuo
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationThe solution was concentrated in vacuo
  6. customthe residue was purified by chromatography (Biotage, 90 g)
  7. washeluting with cyclohexane-EtOAc (2:1)

Sources & evidence

ORD record
ord-c05af71fca0946c8a613bc925fdbd46f
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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