Methyl 4-((1-benzyl-1H-1,2,3-triazol-5-yl)oxy)butanoate → methyl 4-(2H-triazol-4-yloxy)butanoate

HRID 870615Notes

Reaction equation

HRID 870615 reaction equation
C([N:8]1[C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:11][N:10]=[N:9]1)C1C=CC=CC=1>Cl.[Pd].C(O)C>[N:10]1[NH:9][N:8]=[C:12]([O:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:11]=1

Participants

5

Reactant 1

HCID 86726580Methyl 4-((1-benzyl-1H-1,2,3-triazol-5-yl)oxy)butanoate

Product 1

HCID 86726579methyl 4-(2H-triazol-4-yloxy)butanoateYield 99.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Add 5 drops of concentrated hydrochloric acid to a heterogeneous solution of methyl 4-[(1-benzyl-1H-1,2,3-triazol-5-yl)oxy]butanoate (0.50 g; 1.0 equiv; 1.82 mmoles) and 10% palladium on carbon (0.05 g; 0.025 equiv; 0.047 mmoles) in ethanol (7 mL). Evacuate and backfill with nitrogen (3×) then hydrogen (3×), and vigorously stir the reaction mixture for 16 hours under 50 psi hydrogen. Filter the contents and concentrate the filtrate to afford methyl 4-(2H-triazol-4-yloxy)butanoate (0.335 g; 99%). MS (m/z): 184(M−1).

Workup

  1. customEvacuate and backfill with nitrogen (3×)
  2. filtrationFilter the contents
  3. concentrationconcentrate the filtrate

Sources & evidence

ORD record
ord-02492d15e5c044929b41497b795e5aed
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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