Sesamol → 2-(Benzo[d][1,3]dioxol-5-yloxy)pyridine

HRID 1758004Notes

Reaction equation

HRID 1758004 reaction equation
CC([O-])(C)C.[K+].[CH2:7]1[O:15][C:14]2[CH:13]=[CH:12][C:11]([OH:16])=[CH:10][C:9]=2[O:8]1.[K].C(S([C:23]1[CH:28]=[CH:27][C:26](S(CC)(=O)=O)=[CH:25][N:24]=1)(=O)=O)C>CS(C)=O.C1COCC1>[CH2:7]1[O:15][C:14]2[CH:13]=[CH:12][C:11]([O:16][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:10][C:9]=2[O:8]1

Participants

7

Reactant 4

HCID 68289SesamolHCID 5462222PotassiumHCID 132780152,5-Bis(ethylsulfonyl)pyridineHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 1317129492-(Benzo[d][1,3]dioxol-5-yloxy)pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a reaction flask was weighed 5.6 g of t-BuOK and then 50 ml of THF was added. In 50 ml of DMSO was dissolved 6.2 g of 3,4-methylenedioxyphenol which was then slowly added to the t-BuOK solution with stirring. To the resulting potassium phenate solution was added 10.5 g of 2,5-bis(ethylsulfonyl)pyridine and this mixture heated at 50°-55° C. for 3 hrs. After cooling, the reaction mixture was poured into 400 g of ice, stirred and then filtered. The solid which was recovered was dissolved in CH2Cl2, treated with charcoal, dried over MgSO4 and then filtered. The CH2Cl2 solution was concentrated to 50 ml, diluted with an equal volume of hexane and then chilled and a crystalline material recovered, which provided 9.9 g, (80% yield), of 5-ethylsulfonyl)-2-(3,4-methylenedioxyphenoxy)pyridine, m.p. 97°-99° C.

Workup

  1. customInto a reaction flask was weighed
  2. temperaturethis mixture heated at 50°-55° C. for 3 hrs
  3. temperatureAfter cooling
  4. stirringstirred
  5. filtrationfiltered
  6. customThe solid which was recovered
  7. dissolutionwas dissolved in CH2Cl2
  8. additiontreated with charcoal
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationThe CH2Cl2 solution was concentrated to 50 ml
  12. additiondiluted with an equal volume of hexane
  13. temperaturechilled
  14. customa crystalline material recovered

Sources & evidence

ORD record
ord-0e6c54c96f5e440193aa6b3c387e9f0a
Source dataset
uspto-grants-1983_02
Patent number
US04371537

Reaction notes

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