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

HRID 460670Notes

Reaction equation

HRID 460670 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-71e9c9544f9e439cb7120393146991a5
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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