Potassium Carbonate → (S)-alpha-(2'-(2,3-epoxypropan-1-yloxy)benzylidene)-gamma-butyrolactone

HRID 2085225Notes

Reaction equation

HRID 2085225 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH:4]=[C:5]1[CH2:10][CH2:9][O:8][C:6]1=[O:7].C(=O)([O-])[O-].[K+].[K+].S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:25][C@H:26]1[O:28][CH2:27]1)(=O)=O>CN(C)C=O>[O:28]1[CH2:27][C@H:26]1[CH2:25][O:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH:4]=[C:5]1[CH2:10][CH2:9][O:8][C:6]1=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2297583-(2-Hydroxybenzylidene)dihydrofuran-2(3h)-oneHCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoate

Product 1

HCID 86585643(S)-alpha-(2'-(2,3-epoxypropan-1-yloxy)benzylidene)-gamma-butyrolactoneYield 70.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To α-(2′-hydroxybenzylidene)-γ-butyrolactone (60 g) were added dimethylformamide (600 ml) and potassium carbonate (87 g) and (S)-glycidyl nosylate (82 g) was added. The reaction mixture was stirred for 2 days at room temperature. The reaction mixture was concentrated under reduced pressure and water was added. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained crystals were recrystallized from ethyl acetate to give the title compound (55 g), melting point 68-70° C.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure and water
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ec95c0c212214a49a780d89fc39ea472
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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