Trityl chloride → (1-trityl-1H-1,2,4-triazol-3-yl)methanol

HRID 1458581Notes

Reaction equation

HRID 1458581 reaction equation
C(N(CC)CC)C.[OH:8][CH2:9][C:10]1[N:14]=[CH:13][NH:12][N:11]=1.[C:15](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl.O1CCCC1>[OH:8][CH2:9][C:10]1[N:14]=[CH:13][N:12]([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:11]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178519999HCID 178519999, compound

Product 1

HCID 13471694(1-trityl-1H-1,2,4-triazol-3-yl)methanolYield 112.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (1.13 ml, 8.08 mmol) was added to a suspension of 3-hydroxymethyl-1 H- 1, 2,4-triazole [J Am Chem Soc, 77, 1538 (1955)], (400 mg, 4.04 mmol) in dry dichloromethane (8 ml) at 0° C. A solution of trityl chloride (1.24 g, 4.44 mmol) in anhydrous tetrahydrofuran was added, and the mixture was stirred at room temperature for 3 h. The mixture was partitioned between water (75 ml) and dichloromethane (75 ml). The organic layer was dried (MgSO4) and concentrated under reduced pressure to give the title compound (1.547 g, >100%) which was used without purification.

Workup

  1. customThe mixture was partitioned between water (75 ml) and dichloromethane (75 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-baa49eea45614e138c25fabf484bef92
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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