Trifluoroacetic acid → (2-Chloro-phenyl)-(3-hydroxy-pyridin-2-yl)-methanone

HRID 2251988Notes

Reaction equation

HRID 2251988 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([C:17]1[C:22]([O:23]COCC[Si](C)(C)C)=[CH:21][CH:20]=[CH:19][N:18]=1)=[O:16]>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([C:17]1[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][N:18]=1)=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69153886(2-Chloro-phenyl)-[3-(2-trimethylsilanyl-ethoxymethoxy)-pyridin-2-yl]-methanone

Product 1

HCID 69154628(2-Chloro-phenyl)-(3-hydroxy-pyridin-2-yl)-methanoneYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (5 mL) to a solution of (2-chloro-phenyl)-[3-(2-trimethylsilanyl-ethoxymethoxy)-pyridin-2-yl]-methanone (195 mg, 0.54 mmol) in CH2Cl2 (3 mL), stir for 30 minutes. Concentrate; dissolve in 20% i-PrOH/CHCl3, wash with saturated NaHCO3 solution (×2). Dry the combined organic layers over MgSO4 and concentrate. Purify the residue by flash chromatography on silica gel eluting with 0-30% Et2O/hexanes to afford the title compound (102 mg, 82%) as white solid. MS(IS) 233.9 (M+1). TLC: Rf=0.20 (25% Et2O/hexanes).

Workup

  1. concentrationConcentrate
  2. dissolutiondissolve in 20% i-PrOH/CHCl3
  3. washwash with saturated NaHCO3 solution (×2)
  4. dry with materialDry the combined organic layers over MgSO4
  5. concentrationconcentrate
  6. customPurify the residue by flash chromatography on silica gel eluting with 0-30% Et2O/hexanes

Sources & evidence

ORD record
ord-be369d308a2d4d968dd8ea0bd68f9a05
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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