Sodium sulfate decahydrate → (1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methanol

HRID 1171747Notes

Reaction equation

HRID 1171747 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:25]=[CH:24][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([C:19](OCC)=[O:20])[N:16]=[N:15]2)=[CH:11][CH:10]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([CH2:19][OH:20])[N:16]=[N:15]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 12937510Ethyl 1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 23139019(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methanolYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To tetrahydrofuran (THF, 500 ml) was added carefully lithium aluminium hydride (7.3 g) with stirring. The resulting mixture was stirred at 0° C., to which was added dropwise a solution of ethyl 1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylate (50.0 g) in THF (500 ml). The resulting mixture was stirred at room temperature for 30 minutes, and the reaction was stopped by careful addition of sodium sulfate decahydrate. The slurry mixture was stirred at room temperature for 2 hours further, filtered to remove solids, and the filtrate was concentrated in vacuo to afford [1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]methanol (39.51 g, yield: 94%).

Workup

  1. stirringThe resulting mixture was stirred at 0° C., to which
  2. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  3. stirringThe slurry mixture was stirred at room temperature for 2 hours further
  4. filtrationfiltered
  5. customto remove solids
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0e24035e59704a1cb6a00b653555bfbb
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

Loading…