Phenylacetylene → 3-(5-phenyl-1H-1,2,3-triazol-1-yl)propan-1-ol

HRID 387409Notes

Reaction equation

HRID 387409 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][OH:7])=[N+:2]=[N-:3].[C:8]1([C:14]#[CH:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C[C-]1C(C)=C(C)C(C)=C1C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Ru+].C1COCC1>[C:8]1([C:14]2[N:1]([CH2:4][CH2:5][CH2:6][OH:7])[N:2]=[N:3][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 109969743-Azidopropan-1-ol

Product 1

HCID 684330103-(5-phenyl-1H-1,2,3-triazol-1-yl)propan-1-olYield 82%

Reagents, catalysts & solvents 2

HCID 71310463Chlororuthenium(1+) 1,2,3,4,5-pentamethylcyclopenta-2,4-dien-1-ide--triphenylphosphane (1/1/2)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-Azidopropanol (101 mg, 1 mmol), phenylacetylene (113 mg, 1.1 mmol), Cp*RuCl(PPh3)2 (8 mg, 0.01 mmol, 1 mol %). Solvent: THF, 10 mL, 60° C., 2 hours. White microcrystalline product was obtained in 82% yield (167 mg). ESI-MS: m/z 204, [M+H].

Workup

  1. customWhite microcrystalline product was obtained in 82% yield (167 mg)

Sources & evidence

ORD record
ord-f3bf58b128aa4a3787c79de7716ff772
Source dataset
uspto-grants-2013_02
Patent number
US08372986B2

Reaction notes

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