Sodium periodate → 2-Ethyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazole-3-carbaldehyde

HRID 1054925Notes

Reaction equation

HRID 1054925 reaction equation
[CH2:1]([N:3]1[C:7]([CH:8]=C(C)C)=[N:6][C:5]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:4]1)[CH3:2].I([O-])(=O)(=O)=[O:18].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[CH2:1]([N:3]1[C:7]([CH:8]=[O:18])=[N:6][C:5]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:4]1)[CH3:2]

Participants

8

Reactant 2

HCID 23667635Sodium periodateHCID 900179801-ethyl-5-(2-methyl-propenyl)-3-pyrrolidin-1-yl-1H-[1,2,4]triazole

Product 1

HCID 900169032-Ethyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazole-3-carbaldehydeYield 69.2%

Reagents, catalysts & solvents 5

HCID 30318Osmium TetroxideCatalystHCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-ethyl-5-(2-methylprop-1-enyl)-3-(pyrrolidin-1-yl)-1H-1,2,4-triazole (441 mg, 2.00 mmol, Eq: 1.00), osmium(VIII) oxide (382 mg, 382 μl, 60.1 μmol, Eq: 0.03), sodium periodate (1.71 g, 8.01 mmol, Eq: 4) and benzyltriethylammonium chloride (182 mg, 801 μmol, Eq: 0.4) in dioxane (21 ml) and water (6.3 ml) was stirred for 2 hours at 120° C. The mixture was diluted with ethyl acetate and washed with 2× water and brine. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated affording 2-Ethyl-5-pyrrolidin-1-yl-2H-[1,2,4]triazole-3-carbaldehyde (268 mg/69.2%) as a dark green viscous oil. MS: m/e=195.4 (M+H+)

Workup

  1. washwashed with 2× water and brine
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. customevaporated

Sources & evidence

ORD record
ord-f82b9fe615a3414fbee862b4a5b6bf7f
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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