2-(4-Oxoazetidin-2-yl)ethenyl acetate → 2-(4-Oxoazetidin-2-yl)ethyl acetate

HRID 371270Notes

Reaction equation

HRID 371270 reaction equation
[C:1]([O:4][CH:5]=[CH:6][CH:7]1[NH:10][C:9](=[O:11])[CH2:8]1)(=[O:3])[CH3:2]>[Pd].C(OC(=O)C)C>[C:1]([O:4][CH2:5][CH2:6][CH:7]1[NH:10][C:9](=[O:11])[CH2:8]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 541779342-(4-Oxoazetidin-2-yl)ethenyl acetate

Product 1

HCID 127692252-(4-Oxoazetidin-2-yl)ethyl acetateYield 101.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(2-acetoxyvinyl)-azetidin-2-one (3.00 g), 10% Pd/C (0.15 g) and ethylacetate (EtOAc) (120 ml) is hydrogenated in a 500 ml glass bomb on a Parr shaker at an initial pressure of 39 psi. After shaking 10 mins (final pressure of 20 psi), the mixture is filtered through a pad of MgSO4 to remove the catalyst. The filtrate is concentrated in vacuo and the residue stripped with anhydrous benzene to provide 4-(2-acetoxyethyl)-azetidin-2-one (3.098 g) as a clear oil: ir(neat) 3.01, 5.66, 5.75, 7.28, 8.05, and 9.61 cm-1 ; nmr(CDCl3)δ 1.95 (m, 2), 2.07 (s,3), 2.60 (m, 1), 3.12 (m, 1), 3.70 (m, 1), 4.15 (m, 2), and 6.77 (br s, 1).

Workup

  1. filtrationis filtered through a pad of MgSO4
  2. customto remove the catalyst
  3. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-9e822d86bcb749839cc884f9045669de
Source dataset
uspto-grants-1985_07
Patent number
US04530841

Reaction notes

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