Sodium hydride → HCID 21474799, compound

HRID 2294369Notes

Reaction equation

HRID 2294369 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][CH2:8][CH:9]1[O:13][C:12](=[O:14])[NH:11][CH2:10]1.Br[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][CH2:8][CH:9]1[O:13][C:12](=[O:14])[N:11]([CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:10]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 21474759HCID 21474759, compound

Product 1

HCID 21474799HCID 21474799, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 4 was repeated, except that 0.52 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 30 ml of anhydrous dimethylformamide, 2.00 g of 5-(3-chlorophenoxymethyl)oxazolidin-2-one and 2.34 g of ethyl 4-bromobutyrate were used, to give 1.50 g of the title compound having an Rf value of 0.39 (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-00ff3673f15c4ebfa1ee5576897dd264
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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