Tetrabutylammonium Fluoride → (1H-benzimidazol-2-yl)-(2,6-difluoro-3-methoxyphenyl)methanol

HRID 572897Notes

Reaction equation

HRID 572897 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([F:10])[C:3]=1[CH:11]([C:13]1[N:17](COCC[Si](C)(C)C)[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[N:14]=1)[OH:12].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH:14]1[C:15]2[CH:29]=[CH:28][CH:27]=[CH:26][C:16]=2[N:17]=[C:13]1[CH:11]([C:3]1[C:4]([F:10])=[CH:5][CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[F:1])[OH:12]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66836061(2,6-difluoro-3-methoxyphenyl)[1-(2-trimethylsilylethoxymethyl)-1H-benzimidazol-2-yl]methanol

Product 1

HCID 66836022(1H-benzimidazol-2-yl)-(2,6-difluoro-3-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (2,6-difluoro-3-methoxyphenyl)[1-(2-trimethylsilylethoxymethyl)-1H-benzimidazol-2-yl]methanol (1.4 g) in tetrahydrofuran (20 mL) is refluxed for 15 h with tetrabutylammonium fluoride (10 mL of a 1M solution in tetrahydrofuran). The mixture is then concentrated under reduced pressure and purified by chromatography over silica gel (gradient dichloromethane/methanol from 100/0 to 95/5) to afford the pure (1H-benzimidazol-2-yl)-(2,6-difluoro-3-methoxyphenyl)methanol.

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. custompurified by chromatography over silica gel (gradient dichloromethane/methanol from 100/0 to 95/5)

Sources & evidence

ORD record
ord-d33cf9749b6e43969cd426b68e6641eb
Source dataset
uspto-grants-2015_05
Patent number
US09029357B2

Reaction notes

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