Sodium hydride → Ethyl 3-(5-phenoxymethyl-2-oxooxazolidin-3-yl)propionate

HRID 1901752Notes

Reaction equation

HRID 1901752 reaction equation
[H-].[Na+].[O:3]([CH2:10][CH:11]1[O:15][C:14](=[O:16])[NH:13][CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C)C=O>[O:3]([CH2:10][CH:11]1[O:15][C:14](=[O:16])[N:13]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 68320Ethyl 3-bromopropionateHCID 157171415-(Phenoxymethyl)-1,3-oxazolidin-2-one

Product 1

HCID 21474742Ethyl 3-(5-phenoxymethyl-2-oxooxazolidin-3-yl)propionateYield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 4 was repeated, except that 113 mg of sodium hydride (as a 55% by weight dispersion in mineral oil), 10 ml of anhydrous dimethylformamide, 420 mg of 5-phenoxymethyloxazolidin-2-one (prepared as described in Preparation 112) and 471 mg of ethyl 3-bromopropionate were used, to give 463 mg of the title compound having an Rf value of 0.34 (on silica gel thin layer chromatography, using a 2:1 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 4

Sources & evidence

ORD record
ord-2e3a43e5c6694be2b6f077fa43165ac2
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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