Ammonium tetrafluoride → 1-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol

HRID 573150Notes

Reaction equation

HRID 573150 reaction equation
C([Si](C)(C)[O:6][C:7]1[C:15]2[N:14]=[N:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1)(C)(C)C.[F-].[NH4+].[NH4+].[NH4+].[NH4+].[F-].[F-].[F-]>O1CCCC1>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([OH:6])[C:15]=3[N:14]=[N:13]2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 22393694Ammonium tetrafluorideHCID 672271234-(Tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyl)-1h-benzotriazole

Product 1

HCID 1363439141-(4-methoxybenzyl)-1H-1,2,3-benzotriazol-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 342B (2.59 g) in tetrahydrofuran (40 mL) was added tetraammonium fluoride (1M in tetrahydrofuran, 21.03 mL). The solution was mixed at room temperature for two hours. The solvent was removed under vacuum, the residue was taken up in ethyl acetate, and the solution was vacuum filtered over a pad of silica gel. The filtrate was concentrated and purified by flash column chromatography on silica gel using 35% ethyl acetate in hexanes.

Workup

  1. additionThe solution was mixed at room temperature for two hours
  2. customThe solvent was removed under vacuum
  3. filtrationfiltered over a pad of silica gel
  4. concentrationThe filtrate was concentrated
  5. custompurified by flash column chromatography on silica gel using 35% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8debbaad20764ce586193bb01bc33f37
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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