Sodium ethoxide → 2-(Ethoxymethyl)morpholine

HRID 373921Notes

Reaction equation

HRID 373921 reaction equation
Cl.C([N:9]1[CH2:14][CH2:13][O:12][CH:11]([CH2:15][O:16]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:10]1)C1C=CC=CC=1.[O-][CH2:28][CH3:29].[Na+]>C(O)C>[CH2:28]([O:16][CH2:15][CH:11]1[O:12][CH2:13][CH2:14][NH:9][CH2:10]1)[CH3:29]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 19777231HCID 19777231, compound

Product 1

HCID 197772592-(Ethoxymethyl)morpholineYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

4-Benzyl-2-(p-toluenesulfonyloxymethyl)morpholine hydrochloride [cf. Reference Example 11-(1)] (3 g) and sodium ethoxide (2 g) are added to ethanol (150 ml), and the mixture is stirred at 70° C. for 24 hours. The reaction mixture is concentrated under reduced pressure, and to the residue is added saturated aqueous sodium hydrogen carbonate, and the mixture is extracted with ethyl acetate. The extract is washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (eluted by chloroform-methanol=40:1) and further subjected to bulb-to-bulb distillation (at 162° C., 0.4 mmHg) to give the title compound (0.9 g) as colorless liquid.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. additionto the residue is added saturated aqueous sodium hydrogen carbonate
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe extract is washed with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography (eluted by chloroform-methanol=40:1)
  9. distillationfurther subjected to bulb-to-bulb distillation (at 162° C., 0.4 mmHg)

Sources & evidence

ORD record
ord-dc104edd89cc47299b4a1eed51a752ff
Source dataset
uspto-grants-1992_11
Patent number
US05166203

Reaction notes

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