Methanol → HCID 178519906, compound

HRID 485175Notes

Reaction equation

HRID 485175 reaction equation
CC1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[NH:23][N:22]=[N:21][N:20]=4)=[CH:15][CH:14]=3)[C:5]=2[CH:6]=1.C[OH:25]>CN(C)C=O>[CH:6]([C:5]1[C:4]([OH:3])=[CH:10][CH:9]=[CH:8][C:7]=1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[NH:20][N:21]=[N:22][N:23]=2)=[CH:15][CH:14]=1)=[O:25]

Participants

4

Reactant 2

HCID 887MethanolHCID 178422231HCID 178422231, compound

Product 1

HCID 178519906HCID 178519906, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-65 °C

Procedure

5-[4-(2-Methyl-4-benzofuranyloxymethyl)phenyl]tetrazole (1.224 g, 0.004 M) was dissolved in a mixture of dry methanol (130 ml) and dry dimethylformamide (20 ml), and cooled to -65° C. with stirring and exclusion of moisture. Ozonised air was bubbled through the solution at a rate of 20 liters/hr for 1 hr. Nitrogen was then bubbled through the solution (5 mins). to remove excess ozone before the addition of dimethyl sulphide (1.2 ml). The mixture was allowed to warm to room temperature overnight (16 hr). The solvent was removed in vacuo and the residual oil dissolved in ethyl acetate and washed with 2 N hydrochloric acid, water, and extracted with sodium bicarbonate solution. The combined extracts were acidified with 2 N hydrochloric acid to give a solid which was filtered off and dried. This mixture of 5-[4-(2-formyl-3-hydroxyphenoxymethyl)phenyl]tetrazole and 5-[4-(3-acetoxy-2-formylphenoxymethyl)phenyl]tetrazole was suspended in 95% ethanol (20 ml) and 1N sodium hydroxide (20 ml) and stirred at room temperature (1 hr). The solution was evaporated and the residue diluted with water and acidified. The resulting solid was filtered off, washed with water, dried and recrystallised form ethanol/water to give 5-[4-(2-formyl-3-hydroxyphenoxymethyl)phenyl]tetrazole as the 0.5 hydrate, m.p. 206°-206.5° C. (Found: C, 59.00; H, 4.29; N, 18.46. C15H12N4O3 0.5H2O requires C, 59.01; H, 4.29; N, 18.35%).

Workup

  1. customwas bubbled through the solution at a rate of 20 liters/hr for 1 hr
  2. customNitrogen was then bubbled through the solution (5 mins)
  3. customto remove excess ozone
  4. additionbefore the addition of dimethyl sulphide (1.2 ml)
  5. temperatureto warm to room temperature overnight (16 hr)
  6. customThe solvent was removed in vacuo
  7. dissolutionthe residual oil dissolved in ethyl acetate
  8. washwashed with 2 N hydrochloric acid, water
  9. extractionextracted with sodium bicarbonate solution
  10. customto give a solid which
  11. filtrationwas filtered off
  12. customdried
  13. additionThis mixture of 5-[4-(2-formyl-3-hydroxyphenoxymethyl)phenyl]tetrazole and 5-[4-(3-acetoxy-2-formylphenoxymethyl)phenyl]tetrazole
  14. stirring1N sodium hydroxide (20 ml) and stirred at room temperature (1 hr)
  15. customThe solution was evaporated
  16. additionthe residue diluted with water
  17. filtrationThe resulting solid was filtered off
  18. washwashed with water
  19. customdried
  20. customrecrystallised
  21. customform ethanol/water

Sources & evidence

ORD record
ord-40720b5100c247ce98ff277bba550bdc
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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