Formaldehyde → (1-ethyl-1H-1,2,4-triazol-5-yl)methanol
Reaction equation
[CH2:1]([N:3]1[CH:7]=[N:6][CH:5]=[N:4]1)[CH3:2].[CH2:8]=[O:9]>ClCCl>[CH2:1]([N:3]1[C:7]([CH2:8][OH:9])=[N:6][CH:5]=[N:4]1)[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
A mixture of 18a (0.5 g, 5.1 mmol) and paraformaldehyde (0.8 g) were heated at 170° C. for 2 hr under microwave irradiation in a 10-mL tube. The mixture was cooled to room temperature and diluted with dichloromethane (10 mL). The solid was removed by filtration and the filtrate was concentrated under reduced pressure. Two runs (total of 10.3 mmol) were combined and the crude product was purified on an Analogix automated column chromatography system (24 g column, 0-4% MeOH/dichloromethane) to give 410 mg of 26a as a white solid.
Workup
- temperatureThe mixture was cooled to room temperature
- customThe solid was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customthe crude product was purified on an Analogix automated column chromatography system (24 g column, 0-4% MeOH/dichloromethane)
Sources & evidence
- ORD record
- ord-df0240a9746e48d5869552fa4a61adf4
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501738B2
Reaction notes
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