2-Methylpyridine → HCID 12857973, compound

HRID 1736478Notes

Reaction equation

HRID 1736478 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].C([Li])CCC.[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]([OH:18])[CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 79752-MethylpyridineHCID 114773-ChlorobenzaldehydeHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 12857973HCID 12857973, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

50 ml of a solution of 5.58 g of 2-picoline in tetrahydrofuran was cooled to -65° C., followed by the dropwise addition thereto of 26.4 ml of a 2.5M solution of n-butyllithium in hexane. The obtained mixture was stirred at a bulk temperature of -50° to -30° C. for 30 minutes, followed by the dropwise addition thereto of 50 ml of a tetrahydrofuran solution of 8.85 g of 3-chlorobenzaldehyde at -50° C. The temperature of the obtained mixture was raised to 0° C. The resulting mixture was cooled, treated with an aqueous solution of ammonium chloride, and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and concentrated (yield: 13.5 g). This concentrate was used in the subsequent step without purification.

Workup

  1. additionfollowed by the dropwise addition
  2. additionfollowed by the dropwise addition
  3. customat -50° C
  4. temperatureThe resulting mixture was cooled
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated (yield: 13.5 g)
  8. customThis concentrate was used in the subsequent step without purification

Sources & evidence

ORD record
ord-e5c162827009447e9bc12c0fabaa7821
Source dataset
uspto-grants-1996_07
Patent number
US05541213

Reaction notes

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