Toluene → 3-[4-(3-Chlorobenzyloxy) phenyl] 5-(1-hydroxyethyl) oxazolidin-2-one

HRID 330496Notes

Reaction equation

HRID 330496 reaction equation
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH2:21][CH:22]([OH:26])[CH:23]([OH:25])[CH3:24])=[CH:16][CH:15]=1.[C:30](=O)([O-])[O:31]CC.CC[O-].[Na+]>CCO>[Cl:8][C:9]1[CH:10]=[C:11]([CH:27]=[CH:28][CH:29]=1)[CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([N:20]2[CH2:21][CH:22]([CH:23]([OH:25])[CH3:24])[O:26][C:30]2=[O:31])=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 2723922Sodium ethoxideHCID 141824341-[4-(3-Chlorobenzyloxy)phenylamino] butane-2,3-diolHCID 21226545CID 21226545

Product 1

HCID 141824353-[4-(3-Chlorobenzyloxy) phenyl] 5-(1-hydroxyethyl) oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

From a solution of 600 ml of toluene containing 33.4 g (0.10 mol) of the mixture obtained in Example 2, 150 ml of solvent is distilled in an argon atmosphere. Then, successively, 15 g (15.5 ml; 0.127 mol) of ethyl carbonate and 3.4 ml of a solution of EtONa in 1M anhydrous EtOH are added. After 4 hrs 30 mins of reflux, the cyclization reaction is complete. The reaction medium is concentrated, then taken up by 300 ml of methyl ethyl ketone. After washing with 2N HCl, then with a saturated NaCl solution, 35 g of brown solid is recovered corresponding to the product expected.

Workup

  1. temperatureAfter 4 hrs 30 mins of reflux
  2. customthe cyclization reaction
  3. concentrationThe reaction medium is concentrated
  4. washAfter washing with 2N HCl
  5. customwith a saturated NaCl solution, 35 g of brown solid is recovered corresponding to the product

Sources & evidence

ORD record
ord-6f1c23a2b9164588ae2d5c364b9fc432
Source dataset
uspto-grants-1990_01
Patent number
US04897409

Reaction notes

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