1-Ethynyl-3-methoxybenzene → HCID 58156649, compound

HRID 2172157Notes

Reaction equation

HRID 2172157 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1)#[CH:2].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[N:24]([C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=1)=[N+:25]=[N-:26]>C(O)(C)(C)C.O>[CH3:10][O:9][C:5]1[CH:4]=[C:3]([C:1]2[N:26]=[N:25][N:24]([C:27]3[CH:28]=[CH:29][C:30]([C:31]([OH:33])=[O:32])=[CH:34][CH:35]=3)[CH:2]=2)[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6407531-Ethynyl-3-methoxybenzeneHCID 30341844-Azidobenzoic acidHCID 23667548Sodium Ascorbate

Product 1

HCID 58156649HCID 58156649, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

To a solution of 1-ethynyl-3-methoxybenzene (396 mg, 3.00 mmol, Aldrich) in 50% tert-butanol/water (4.0 mL) is added 300 μL (0.30 mmol) of an aqueous solution of sodium ascorbate (594 mg in 3 mL H2O), 100 μL (0.030 mmol) of an aqueous CuSO4.5H2O solution (75 mg in 1 mL H2O), followed by 4-azidobenzoic acid (489 mg, 3 mmol). The resulting mixture is stirred for 7 days, the resulting suspension filtered and washed with H2O (3×30 mL), Et2O (2×15 mL), and hexanes (3×30 mL). The solid is dried overnite in vacuo (70° C., 10 torr) to afford 880 mg (99%) of 4-[4-(3-methoxy-phenyl)-[1,2,3]triazol-1-yl]benzoic acid as a pale yellow powder: m.p. 276-277° C. 1H NMR (300 MHz, DMSO-d6) δ 9.44 (s, 1H), 8.16 (d, J=8.5 Hz, 2H), 8.08 (d, J=8.3 Hz, 2H), 7.52 (m, 2H), 7.40 (t, J=7.8 Hz, 1H), 6.95 (ddd, J=8.3, 2.5, 0.8 Hz, 1H), 3.82 (s, 3H). MS m/z 296.29, calcd for C16H13N3O3 (M+H+) 296.

Workup

  1. filtrationthe resulting suspension filtered
  2. washwashed with H2O (3×30 mL), Et2O (2×15 mL), and hexanes (3×30 mL)
  3. customThe solid is dried overnite in vacuo (70° C., 10 torr)

Sources & evidence

ORD record
ord-27fc935b51b942ab98582343e01ca8ee
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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