2-Methylpyridine → HCID 12857973, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence