Water → 2-(1-Propenyloxymethyl)morpholine

HRID 440829Notes

Reaction equation

HRID 440829 reaction equation
[CH2:1]([O:4][CH2:5][CH:6]1[O:11][CH2:10][CH2:9][NH:8][CH2:7]1)[CH:2]=[CH2:3].CC(C)([O-])C.[K+].O>O1CCOCC1>[CH:1]([O:4][CH2:5][CH:6]1[O:11][CH2:10][CH2:9][NH:8][CH2:7]1)=[CH:2][CH3:3]

Participants

5

Procedure

2-(Allyloxymethyl)morpholine (39.5 g, 0.25 mol) was dissolved in 1,4-dioxane (500 ml), and potassium tert-butoxide (28.2 g, 0.25 mol) was added to the solution at room temperature, followed by heating under reflux for 3 hours. After completion of the reaction, water was added to the reaction mixture at room temperature, and the reaction mixture was extracted with chloroform (3×1000 ml). The extract was washed with a saturated aqueous solution of sodium chloride (1000 ml) and dried over magnesium sulfate. The solvent was evaporated to give crude 2-(1-propenyloxymethyl)morpholine (40.0 g) as a pale yellow oily substance.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. additionwas added to the reaction mixture at room temperature
  4. extractionthe reaction mixture was extracted with chloroform (3×1000 ml)
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride (1000 ml)
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-433a069850eb48378f3434745611c334
Source dataset
uspto-grants-1996_05
Patent number
US05521180

Reaction notes

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