3-Hydroxypyridine → HCID 15635484, compound

HRID 2251991Notes

Reaction equation

HRID 2251991 reaction equation
CC(C)([O-])C.[K+].[OH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[CH3:14][Si:15]([CH3:22])([CH3:21])[CH2:16][CH2:17][O:18][CH2:19]Cl>CN(C=O)C.C1COCC1>[CH3:14][Si:15]([CH3:22])([CH3:21])[CH2:16][CH2:17][O:18][CH2:19][O:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 79713-HydroxypyridineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 23665647Potassium tert-butoxide

Product 1

HCID 15635484HCID 15635484, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add potassium tert-butoxide (2.69 g, 24 mmol) to a 0° C. solution of 3-hydroxy-pyridine (1.90 g, 20 mmol) in DMF (30 mL) and THF (30 mL) stirring under N2. Add 2-(trimethylsilyl)ethoxy-methyl chloride (3.72 mL, 21 mmol) dropwise and allow to warm slowly to RT overnight. Add water to quench, stir for 5 minutes and concentrate. Dissolve in 20% i-PrOH/CHCl3, wash with saturated NaHCO3 solution (2×) and brine. Dry the combined organic layers over MgSO4 and concentrate. Purify the residue by flash chromatography on silica gel eluting with 0-50% EtOAc/hexanes to afford the title compound (3.14 g, 70%) as yellow liquid. MS(IS) 226 (M+1). TLC: Rf=0.43 (50% EtOAc/hexanes).

Workup

  1. customAdd water to quench
  2. stirringstir for 5 minutes
  3. concentrationconcentrate
  4. dissolutionDissolve in 20% i-PrOH/CHCl3
  5. washwash with saturated NaHCO3 solution (2×) and brine
  6. dry with materialDry the combined organic layers over MgSO4
  7. concentrationconcentrate
  8. customPurify the residue by flash chromatography on silica gel eluting with 0-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-ca249f4e0292434fa728c19cc979efbf
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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