Sodium hydride → HCID 21830918, compound

HRID 1600809Notes

Reaction equation

HRID 1600809 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=1.Cl.Cl[CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CN(C=O)C>[N:20]1([CH2:19][CH2:18][O:3][C:4]2[CH:5]=[C:6]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]=[CH:8][CH:9]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 572437Ethyl (3-Hydroxyphenyl)acetate

Product 1

HCID 21830918HCID 21830918, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of 97% NaH (1.75 g, 0.07 mol) in DMF (50 mL) was stirred for 15 minutes then ethyl 3-hydoxyphenylacetate (5.4 g, 0.03 mol) in DMF (25 mL) was added. The reaction mixture was stirred for 0.5 hours, then was cooled in an ice bath and N-(2-chloroethyl)morpholine hydrochloride (5.6 g, 0.03 mol) was added. The reaction mixture was at room temperature overnight, then was heated on a steam bath for four hours. The solvent was stripped, the residue was partitioned between cold water and ether, the organic layer was separated, and the aqueous layer was extracted with ether. The organic layers were combined, dried over MgSO4, filtered and stripped to afford crude product which was purified by column chromatography on silica gel eluting with ethyl acetate to afford 4.64 g of ethyl 3-[2-(4-morpholinyl)ethoxy]phenylacetate.

Workup

  1. stirringThe reaction mixture was stirred for 0.5 hours
  2. temperaturewas cooled in an ice bath
  3. waitThe reaction mixture was at room temperature overnight
  4. temperaturewas heated on a steam bath for four hours
  5. customthe residue was partitioned between cold water and ether
  6. customthe organic layer was separated
  7. extractionthe aqueous layer was extracted with ether
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customto afford crude product which
  11. customwas purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-1de910381215468ebbb918b1850ba0d3
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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