Sodium hydride → HCID 53914591, compound

HRID 2225817Notes

Reaction equation

HRID 2225817 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH3:2].[H-].[Na+].Br[CH2:18][C:19]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[O:20]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:20])=[CH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetateHCID 139968762-Bromo-1-(morpholin-4-yl)ethan-1-one

Product 1

HCID 53914591HCID 53914591, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester (0.71 g) in dimethylformamide (7 mL) under argon was treated with 55% sodium hydride (0.16 g), stirred for 15 minutes and then 4-(bromoacetyl)morpholine (0.76 g) in dimethylformamide (5 mL) was added. The mixture was stirred at room temperature for 18 hours and worked up as in Example 20. The crude product was purified by HPLC (toluene-hexane; 3:1 ) and then crystallized twice from ethyl acetate-hexane to provide 0.76 g of 4-[2-(4-morpholinyl)-2-oxoethoxy]-alpha-oxobenzeneacetic acid ethyl ester, mp 103°-106 ° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. customThe crude product was purified by HPLC (toluene-hexane; 3:1 )
  3. customcrystallized twice from ethyl acetate-hexane

Sources & evidence

ORD record
ord-12c45818d67a46209f7757fc2504afe5
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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