HCID 21220956, compound → HCID 21220907, compound

HRID 1584775Notes

Reaction equation

HRID 1584775 reaction equation
[O:1]1CCCO[CH:2]1[C:7]1[C:15]2[O:14][CH:13]=[CH:12][C:11]=2[CH:10]=[C:9]([N:16]2[CH:20]=[C:19]([Si](C)(C)C)[N:18]=[N:17]2)[CH:8]=1>[OH-].[K+].O.CO>[N:16]1([C:9]2[CH:8]=[C:7]([CH:2]=[O:1])[C:15]3[O:14][CH:13]=[CH:12][C:11]=3[CH:10]=2)[CH:20]=[CH:19][N:18]=[N:17]1

Participants

5

Reactant 1

HCID 21220956HCID 21220956, compound

Product 1

HCID 21220907HCID 21220907, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

A solution of 1-(7-[1,3]dioxan-2-yl-benzofuran-5-yl)-4-trimethylsilanyl-1H-[1,2,3]triazole (180 mg) in potassium hydroxide (0.1 g), water (10 ml) and methanol (10 ml) was stirred for 18 h at room temperature. The solvent was removed, diluted with water (10 ml) and extracted with dichloromethane (3×15 ml). The organic extracts were washed with water (10 ml), dried, and evaporated. The residual oil was dissolved in hydrochloric acid (2M; 10 ml) and tetrahydrofuran (10 ml) and stirred at 70° for 30 min. The solution was cooled, basified with 1M sodium carbonate solution and extracted with dichloromethane (3×20 ml). The combined extracts were dried, and evaporated to give the title compound as a pale cream coloured solid (74 mg).

Workup

  1. customThe solvent was removed
  2. additiondiluted with water (10 ml)
  3. extractionextracted with dichloromethane (3×15 ml)
  4. washThe organic extracts were washed with water (10 ml)
  5. customdried
  6. customevaporated
  7. dissolutionThe residual oil was dissolved in hydrochloric acid (2M; 10 ml)
  8. temperatureThe solution was cooled
  9. extractionextracted with dichloromethane (3×20 ml)
  10. customThe combined extracts were dried
  11. customevaporated

Sources & evidence

ORD record
ord-e8b8cb102a4c4c13ae6ccca6b612e0ac
Source dataset
uspto-grants-1999_08
Patent number
US05935972

Reaction notes

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