Ethyl 2-(oxetan-3-ylidene)propanoate → Ethyl 2-(oxetan-3-yl)propanoate

HRID 63536Notes

Reaction equation

HRID 63536 reaction equation
[O:1]1[CH2:4][C:3](=[C:5]([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:2]1>CCO.[Pd]>[O:1]1[CH2:2][CH:3]([CH:5]([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:4]1

Participants

4

Reactant 1

HCID 86698951Ethyl 2-(oxetan-3-ylidene)propanoate

Product 1

HCID 86698952Ethyl 2-(oxetan-3-yl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (i) (151 mg, 0.97 mmol) in EtOH (54 mL) was added 10% Pd/C (50 mg, 0.05 mmol). The reaction was degassed and purged with hydrogen at balloon pressure (×3) then stirred under hydrogen at RT for 16 h. The reaction mixture was filtered and the residue washed with acetonitrile (10 mL). The combined organics were concentrated in vacuo and the residue, (ii) (148 mg), was used without further purification.

Workup

  1. customThe reaction was degassed
  2. custompurged with hydrogen at balloon pressure (×3)
  3. filtrationThe reaction mixture was filtered
  4. washthe residue washed with acetonitrile (10 mL)
  5. concentrationThe combined organics were concentrated in vacuo
  6. customthe residue, (ii) (148 mg), was used without further purification

Sources & evidence

ORD record
ord-fcdbefe96d574def846094b8700ca02b
Source dataset
uspto-grants-2016_09
Patent number
US09447080B2

Reaction notes

Loading…