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

HRID 2085236Notes

Reaction equation

HRID 2085236 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=1[CH2:10][CH:11]1[CH2:16][CH2:15][O:14][C:12]1=[O:13].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][CH:26]1[CH2:25][O:7][C:8]1[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=1[CH2:10][C@H:11]1[CH2:16][CH2:15][O:14][C:12]1=[O:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoateHCID 21813505alpha-(2'-Hydroxybenzyl)-gamma-butyrolactone

Product 1

HCID 21306424(2S)-alpha-(2'-(2,3-Epoxypropan-1-yloxy)benzyl)-gamma-butyrolactoneYield 106.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethylformamide (100 ml) and potassium carbonate (10 g) were added to α-(2′-hydroxybenzyl)-γ-butyrolactone (5.0 g), and (S)-glycidyl nosylate (6 g) was added. The mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure and water was added. The reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (6.1 g).

Workup

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

Sources & evidence

ORD record
ord-d3e0f427f45d4d618c186c919a70ad6c
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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