(1-phenyl-1H-1,2,3-triazol-4-yl)methanol → 1-phenyl-1H-1,2,3-triazole-4-carbaldehyde

HRID 628677Notes

Reaction equation

HRID 628677 reaction equation
[C:1]1([N:7]2[CH:11]=[C:10]([CH2:12][OH:13])[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)Cl.O=[Mn]=O>[C:1]1([N:7]2[CH:11]=[C:10]([CH:12]=[O:13])[N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 708707(1-phenyl-1H-1,2,3-triazol-4-yl)methanol

Product 1

HCID 14786021-phenyl-1H-1,2,3-triazole-4-carbaldehydeYield 82%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-phenyl-1H-1,2,3-triazol-4-yl)methanol, 7, (1.03 g, 5.87 mmol) in CH2Cl2 (50 mL) was added MnO2 (2.05 g, 23.5 mmol). The reaction mixture was stirred for 3 days at room temperature. The reaction mixture was then filtered through Celite® and the resulting filtrate was concentrated in vacuo. The crude material was purified by silica gel chromatography (0-5% methanol/dichloromethane) yielding 0.83 g (82%) of 9: 1H NMR (400 MHz, CDCl3) δ 10.22 (s, 1H), 8.51 (s, 1H), 7.53, (d, J=9.6 Hz, 2H), 7.58-7.49, (m, 3H).

Workup

  1. filtrationThe reaction mixture was then filtered through Celite®
  2. concentrationthe resulting filtrate was concentrated in vacuo
  3. customThe crude material was purified by silica gel chromatography (0-5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-ebe0198a58ad45d9b06852906b0b66b1
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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