Triphenylphosphine → 4-(4-[1,2,3]Triazol-1-yl-but-1-enyl)-phenol

HRID 750971Notes

Reaction equation

HRID 750971 reaction equation
[CH2:1]([N:5]1[CH:9]=[CH:8][N:7]=[N:6]1)[CH2:2][CH:3]=[CH2:4].C([Si]([O:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1)(C)C)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[N:5]1([CH2:1][CH2:2][CH:3]=[CH:4][C:21]2[CH:22]=[CH:23][C:18]([OH:17])=[CH:19][CH:20]=2)[CH:9]=[CH:8][N:7]=[N:6]1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 148035271-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-4-iodobenzeneHCID 190682081-but-3-enyl-1H-[1,2,3]triazole

Product 1

HCID 692918004-(4-[1,2,3]Triazol-1-yl-but-1-enyl)-phenol

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 3.00 g (24.4 mmol) 1-but-3-enyl-1H-[1,2,3]triazole, 6.79 g (20.3 mmol) tert-butyl-(4-iodo-phenoxy)-dimethyl-silane, 1.07 g (4.06 mmol) triphenylphosphine, 0.685 g (3.05 mmol) palladium(II)acetate and 56 ml triethylamine was heated to reflux for 24 h. The reaction mixture was cooled to r.t., evaporated, stirred with ice and adjusted to pH=1 by addition of conc. HCl. The organic material was collected with ethyl acetate/dichloromethane 1:2, the organic phase dried over sodium sulfate and evaporated. The residue was stirred with 20.3 ml 1M solution of tetrabutylammonium fluoride solution in THF at 28° C. for 3 h. After removal of THF, the residue was dissolved in dichloromethane, washed with water, evaporated and purified by chromatography on silica gel (ethyl acetate/n-heptane 5:1). The product containing fractions were collected, evaporated and stirred with little ethyl acetate/n-heptane 3:1 to yield 1.53 g (29%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. customevaporated
  4. additionadjusted to pH=1 by addition of conc. HCl
  5. customThe organic material was collected with ethyl acetate/dichloromethane 1:2
  6. dry with materialthe organic phase dried over sodium sulfate
  7. customevaporated
  8. stirringThe residue was stirred with 20.3 ml 1M solution of tetrabutylammonium fluoride solution in THF at 28° C. for 3 h
  9. customAfter removal of THF
  10. dissolutionthe residue was dissolved in dichloromethane
  11. washwashed with water
  12. customevaporated
  13. custompurified by chromatography on silica gel (ethyl acetate/n-heptane 5:1)
  14. additionThe product containing fractions
  15. customwere collected
  16. customevaporated
  17. stirringstirred with little ethyl acetate/n-heptane 3:1
  18. customto yield 1.53 g (29%)

Sources & evidence

ORD record
ord-0eb27830ab684523ad1a5a413a2c58ed
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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