Tetrahydrofuran → 1-(o-Tolyl)-5-phenyl-triazole

HRID 387411

Reaction equation

HRID 387411 reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([N:7]=[N+:8]=[N-:9])=[CH:3][CH:2]=1.[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:19]1COCC1>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+]>[C:3]1([CH3:19])[CH:2]=[CH:1][CH:6]=[CH:5][C:4]=1[N:7]1[C:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:18][N:9]=[N:8]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10821PhenylacetyleneHCID 1374301-Azido-4-methylbenzene

Product 1

HCID 684326331-(o-Tolyl)-5-phenyl-triazoleYield 51%

Reagents, catalysts & solvents 1

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

Procedure

4-Tolyl azide (133 mg, 1 mmol), phenylacetylene (113 mg, 1.1 mmol), Cp*RuCl(PPh3)2 (16 mg, 0.02 mmol, 2 mol %). Solvent: THF, 10 mL, 60° C., 6 hours. Slightly yellow product obtained in 51% yield (120 mg). ESI-MS: m/z 236, [M+H].

Workup

  1. customSlightly yellow product obtained in 51% yield (120 mg)

Sources & evidence

ORD record
ord-9d4774a15f234d5e8296945ef84477d4
Source dataset
uspto-grants-2013_02
Patent number
US08372986B2

Linked notes

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