Sodium hydride → Methyl 4-[2-(4-morpholinyl)ethoxy]phenylacetate

HRID 1600794Notes

Reaction equation

HRID 1600794 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1.Cl.Cl[CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CN(C=O)C>[N:19]1([CH2:18][CH2:17][O:3][C:4]2[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 21830903Methyl 4-[2-(4-morpholinyl)ethoxy]phenylacetateYield 69.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

97% NaH (3.56 g, 0.14 mol) was suspended in DMF (100 ml) and methyl 4-hydroxyphenylacetate (10 g, 0.06 mol) was added. The reaction mixture was stirred for 0.5 hours, then N-(2-chloroethyl)morpholine hydrochloride (11.2 g) was added and the reaction mixture was stirred at room temperature for about 2 days, and then was heated on a steam bath for 2 hours. The reaction mixture was cooled, filtered and the filtrate was stripped. The residue was partitioned between water and ether, the layers were separated and the aqueous layer was extracted with ether. The organic layers were combined, washed with brine, and dried over MgSO4, filtered and concentrated to afford 11.59 g (69%) of methyl 4-[2-(4-morpholinyl)ethoxy]phenylacetate.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for about 2 days
  2. temperaturewas heated on a steam bath for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customThe residue was partitioned between water and ether
  6. customthe layers were separated
  7. extractionthe aqueous layer was extracted with ether
  8. washwashed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-79007caef6e14f1aaf3a35541db7984f
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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