Methyl iodide → 4-(3-methoxymethoxy-4-methyl-phenyl)-1-methyl-1H-[1,2,3]triazol

HRID 2081078Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[C:5]([O:10][CH2:11][O:12][CH3:13])[CH:4]=1)#[CH:2].I[CH3:15].[N-:16]=[N+:17]=[N-:18].[Na+]>O.C(O)(C)(C)C.[Cu].S([O-])([O-])(=O)=O.[Cu+2]>[CH3:13][O:12][CH2:11][O:10][C:5]1[CH:4]=[C:3]([C:1]2[N:16]=[N:17][N:18]([CH3:15])[CH:2]=2)[CH:8]=[CH:7][C:6]=1[CH3:9]

Participants

Conditions

Temperature: 125 °C

Procedure

To a suspension of 4-ethynyl-2-methoxymethoxy-1-methyl-benzene (0.64 g, 3.63 mmol) (from Example 19 supra), iodomethane (0.23 mL, 3.63 mmol) (Aldrich) and sodium azide (0.24 g, 3.63 mmol) (Aldrich) in a mixture of water (6 mL) and t-butanol (6 mL) was added copper powder (0.17 g, 2.68 mmol) and aqueous copper sulphate solution (1 N, 0.7 mL). The reaction mixture was heated at 125° C. for 20 minutes in a microwave reactor. After cooling, the reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (2×). The combined organic phase was washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography eluting with 5-60% ethyl acetate in hexanes to give 4-(3-methoxymethoxy-4-methyl-phenyl)-1-methyl-1H-[1,2,3]triazol. (Yield 0.57 g, 67%).

Workup

temperatureAfter cooling
customthe reaction mixture was partitioned between ethyl acetate and water
extractionThe aqueous phase was extracted with ethyl acetate (2×)
washThe combined organic phase was washed with water and brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was purified by flash chromatography
washeluting with 5-60% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-2a954c55d3504fb4a8c67731cc9079dd
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932390B2

Reaction notes

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