Tetrahydrofuran → 1-(4-Methylpyridin-2-yl)propan-1-one

HRID 1059904Notes

Reaction equation

HRID 1059904 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N:4]=1)#N.[CH2:10]([Mg]Br)[CH3:11].[Cl-].[NH4+].[O:16]1CCCC1>>[CH3:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([C:1](=[O:16])[CH2:10][CH3:11])[CH:8]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 887392-Cyano-4-methylpyridineHCID 178418443HCID 178418443, compound

Product 1

HCID 186309841-(4-Methylpyridin-2-yl)propan-1-one

Conditions

Temperature
-55 °C

Procedure

To a stirred suspension of 2-cyano-4-methylpyridine (1.0 g) in tetrahydrofuran (10 ml) was added a solution of ethylmagnesium bromide in tetrahydrofuran (0.96M, 9.7 ml) dropwise at −55° C. The reaction mixture was stirred at −55° C. for 30 minutes and warmed to 0° C. Then the mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate twice. The combined organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give 1-(4-methylpyridin-2-yl)-propan-1-one (1.21 g).

Workup

  1. temperaturewarmed to 0° C
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-dde9e40340864043baf96547c8215367
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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