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

HRID 460656Notes

Reaction equation

HRID 460656 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-3dd7a5d4bd4b4d759e7efed18da46a03
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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