Water → 5-(2-Oxiranyl)-1,3-benzodioxole

HRID 274086Notes

Reaction equation

HRID 274086 reaction equation
[CH3:1]C(C)([O-])C.[K+].[I-].C[S+](C)C.[CH:12]1[C:17]([CH:18]=[O:19])=[CH:16][C:15]2[O:20][CH2:21][O:22][C:14]=2[CH:13]=1.O>O1CCCC1.CS(C)=O>[CH2:21]1[O:22][C:14]2[CH:13]=[CH:12][C:17]([CH:18]3[CH2:1][O:19]3)=[CH:16][C:15]=2[O:20]1

Participants

7

Reactant 4

HCID 962WaterHCID 8438PiperonalHCID 75127Trimethylsulfonium iodideHCID 23665647Potassium tert-butoxide

Product 1

HCID 108990185-(2-Oxiranyl)-1,3-benzodioxoleYield 91.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled suspension of potassium tert-butoxide (0.82 g) in tetrahydrofuran (6.6 ml) was added trimethylsulfonium iodide (98% purity; 1.5 g) in dimethyl sulfoxide (6.6 ml). After the addition was complete, piperonal (1.0 g) in tetrahydrofuran (3.3 ml) was added dropwise to the mixture while the internal temperature was maintained below 5° C. After stirring at ambient temperature for 1 hour, the mixture was poured into water and extracted once with ethyl acetate. The extract was washed twice with water and once with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give 3,4-methylenedioxyphenyloxirane (1.0 g), which was used for next reaction without further purification.

Workup

  1. additionAfter the addition
  2. temperaturewas maintained below 5° C
  3. extractionextracted once with ethyl acetate
  4. washThe extract was washed twice with water and once with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d6b9752f2f742e3a4d1cf64cd88669c
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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