Ethyl Acetate → HCID 22217916, compound

HRID 396177Notes

Reaction equation

HRID 396177 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9](CCCO)#[N:10].[CH3:15][Si](C)(C)[N-][Si](C)(C)C.[Na+].CCO[C:28]([CH3:30])=[O:29]>CS(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:29][CH2:28][CH:30]([C:9]#[N:10])[CH3:15])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 693532,5-DibromopyridineHCID 2207054-hydroxybutanenitrileHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 22217916HCID 22217916, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 2,5-dibromopyridine (500 mg, 2.1 mmol) and 3-cyano-1-propanol (270 mg, 3.1 mmol) in DMSO (2 mL) was added 1M sodium hexamethyldisilazide (2.1 mL, 2.1 mmol). The reaction was stirred at room temperature overnight. EtOAc was added to the reaction and the mixture was washed with water (2×10 mL). The EtOAc fraction was dried over anhydrous sodium sulfate and evaporated on a rotary evaporator. The crude product was purified by flash column chromatography over silica gel using 40%EtOAc/hexanes to give 200 mg of 5-bromo-2-cyanopropyloxypyridine as a pale yellow solid (39.3%).

Workup

  1. washthe mixture was washed with water (2×10 mL)
  2. dry with materialThe EtOAc fraction was dried over anhydrous sodium sulfate
  3. customevaporated on a rotary evaporator
  4. customThe crude product was purified by flash column chromatography over silica gel using 40%EtOAc/hexanes

Sources & evidence

ORD record
ord-2a998d62cdf34079b3e5dba69ac11ea9
Source dataset
uspto-grants-2003_08
Patent number
US06608052B2

Reaction notes

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