Ethyl Acrylate → Ethyl 4-(3-ethoxy-3-oxopropyl)morpholine-2-carboxylate

HRID 1471426Notes

Reaction equation

HRID 1471426 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14]>CCOCC>[CH2:17]([O:16][C:12](=[O:15])[CH2:13][CH2:14][N:1]1[CH2:6][CH2:5][O:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1)[CH3:18]

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 15651197Ethyl morpholine-2-carboxylate

Product 1

HCID 15651198Ethyl 4-(3-ethoxy-3-oxopropyl)morpholine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl morpholine-2-carboxylate (3 g, 18.85 mmol) and ethyl acrylate (5 ml, 18.85 mmol) was heated at 100° C. for 14 h. The reaction was cooled to RT then diluted with Et2O and extracted with aqueous 3M HCl. The combined aqueous layers were basified by solid K2CO3 and extracted with DCM. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound as a pale-yellow oil, which was used without further purification.

Workup

  1. temperatureThe reaction was cooled to RT
  2. extractionextracted with aqueous 3M HCl
  3. extractionextracted with DCM
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-33ad05b0ab804b288b8aa1dd0e10474b
Source dataset
uspto-grants-2015_04
Patent number
US09012447B2

Reaction notes

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