Methyl Acrylate → HCID 21621270, compound

HRID 979258Notes

Reaction equation

HRID 979258 reaction equation
[CH2:1]([N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19].CC(C)([O-])C.[K+]>O1CCCC1>[CH3:22][O:21][C:17](=[O:20])[CH2:18][CH2:19][O:9][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 69297DibenzylhydroxylamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 21621270HCID 21621270, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 42.6 g of N,N-dibenzylhydroxylamine, 25.8 g of methyl acrylate and 2.0 g of potassium-tert-butoxide in 200 ml of tetrahydrofuran is heated under reflux for 12 hours under N2. The crude reaction mixture is concentrated under reduced pressure and the residue is partitioned between water and ether. The orcanic layer is washed with water, saturated NaHSO4 solution and brine, dried (MgSO4) and then evaporated under reduced pressure to give the title compound as an oil.

Workup

  1. temperatureunder reflux for 12 hours under N2
  2. customThe crude reaction mixture
  3. concentrationis concentrated under reduced pressure
  4. customthe residue is partitioned between water and ether
  5. washThe orcanic layer is washed with water, saturated NaHSO4 solution and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-55086bda318e429d99808034e1a1d662
Source dataset
uspto-grants-1987_05
Patent number
US04666962

Reaction notes

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