Tributylphosphine → 1-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-ethanone

HRID 424798Notes

Reaction equation

HRID 424798 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[N:20]1[C:24]([CH2:25]O)=[C:23]([CH:27]([CH3:29])[CH3:28])[N:22]=[N:21]1.C(P(CCCC)CCCC)CCC.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1(C)C=CC=CC=1>[Cl:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[C:14]=1[N:20]1[C:24]([CH2:25][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([CH3:11])[CH:3]=2)=[C:23]([CH:27]([CH3:29])[CH3:28])[N:22]=[N:21]1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 701334-Hydroxy-2-methylacetophenoneHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 45790389(1-(2,6-dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methanol

Product 1

HCID 667040541-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-ethanoneYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 0° C. suspension of 4′-hydroxy-2′-methylacetophenone (969 mg, 6.45 mmol), [3-(2,6-Dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-yl]-methanol (1.85 g, 6.45 mmol), tri-n-butylphosphine (2.42 ml, 9.73 mmol) in toluene (20 mL) is added ADDP (2.46 g, 9.73 mmol). The reaction mixture is warmed to room temperature and stirred overnight. The reaction mixture is concentrated and the residue is chromatographed eluting with 0% to 30% EtOAc/Hex to yield the title compound (1.71 mg, 63%). 1H NMR (400 MHz, CDCl3) δ 7.75 (dd, 1H, J=8.5, 2.1 Hz), 7.72 (d, 1H, J=1.3 Hz), 7.49 (d, 1H, J=2.2 Hz), 7.47 (s, 1H), 7.41 (dd, 1H, J=9.2, 6.6 Hz), 6.78 (d, 1H, J=8.4 Hz), 4.99 (s, 2H), 3.22 (sept, 1H, J=7.0 Hz), 2.52 (s, 3H), 2.06 (s, 3H), 1.46 (d, 6H, J=7.0 Hz).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is chromatographed
  3. washeluting with 0% to 30% EtOAc/Hex

Sources & evidence

ORD record
ord-e907547d825d4b7fb4dac26acb048816
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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