Methyl 2-oxo-3-phenylpropanoate → 5-[2-(Benzyloxy)ethyl]-3-hydroxy-4-phenylfuran-2(5H)-one

HRID 2291627Notes

Reaction equation

HRID 2291627 reaction equation
[O:1]=[C:2]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH3:6])=[O:4].[CH2:14]([O:21][CH2:22][CH2:23]C=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[OH:1][C:2]1[C:3](=[O:4])[O:5][CH:6]([CH2:23][CH2:22][O:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 562359Methyl 2-oxo-3-phenylpropanoateHCID 108882613-(Benzyloxy)propanal

Product 1

HCID 139072715-[2-(Benzyloxy)ethyl]-3-hydroxy-4-phenylfuran-2(5H)-oneYield 68.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-oxo-3-phenylpropionate (2.0 g) and 3-benzyloxypropanal (1.84 g) in N,N-dimethylformamide (40 ml) was dropwise added 1,8-diazabicyclo[5.4.0]undecen-7 (1.76 ml) at 0° C. with stirring. The mixture was stirred at the same temperature for 2 hours PG,28 and the solvent was evaporated. The residue was added to diluted hydrochloric acid and extracted with diethyl ether. The extract was washed with water, dried and evaporated in vacuo. The residue was recrystallized from diisopropyl ether to give 3-hydroxy-4-phenyl-5(2-benzyloxyethyl)-2(5H)furanone (2.39 g).

Workup

  1. customat 0° C.
  2. stirringThe mixture was stirred at the same temperature for 2 hours PG,28
  3. customthe solvent was evaporated
  4. additionThe residue was added to diluted hydrochloric acid
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with water
  7. customdried
  8. customevaporated in vacuo
  9. customThe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-2211b2c274274ea28c0906a4905a92f0
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

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