[2-(1-benzyl-1H-1,2,3-triazol-5-yl)ethoxy]acetic acid → HCID 178525980, compound

HRID 870560Notes

Reaction equation

HRID 870560 reaction equation
[H][H].C([N:10]1[C:14]([CH2:15][CH2:16][O:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:13][N:12]=[N:11]1)C1C=CC=CC=1>C(O)(C)C.O.[Pd](Cl)Cl>[NH:10]1[C:14]([CH2:15][CH2:16][O:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:13][N:12]=[N:11]1

Participants

6

Reactant 2

HCID 86726526[2-(1-benzyl-1H-1,2,3-triazol-5-yl)ethoxy]acetic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 178525980HCID 178525980, compoundYield 120.3%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Pressurize 1 atmosphere of hydrogen (g) to a flask containing [2-(1-benzyl-1H-1,2,3-triazol-5-yl)ethoxy]acetic acid (10.1 g; 1.00 equiv; 38.66 mmoles) and palladium (II) chloride (3 g; 16.92 mmoles; 3.00 g) in isopropyl alcohol (300 mL) and water (60 mL). Maintain the flask under a hydrogen atmosphere for 3 h, then filter through Celite™ and concentrate. Add toluene (2×50 mL) and concentrate to afford the title compound (7.96 g, 100%). 1H NMR (d6-DMSO): 2.86 (t, J=7 Hz, 2H), 3.65 (t, J=7 Hz, 2H), 3.98 (s, 2H), 7.77 (s, 1H), 13.4-13.6 (br s, 2H).

Workup

  1. temperatureMaintain the flask under a hydrogen atmosphere for 3 h
  2. filtrationfilter through Celite™
  3. concentrationconcentrate
  4. concentrationAdd toluene (2×50 mL) and concentrate

Sources & evidence

ORD record
ord-c5f6f851b8fb43cb87e7f35517c431dc
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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