反应详情

温度

-75 °C

To a suspension of (bromomethyl)triphenylphosphonium bromide (3.06 g, 7.01 mmol) in 30 mL of THF, potassium tert-butoxide (0.78 g, 7.01 mmol) was added portionwise at −75° C. under argon. After completion of the addition, the mixture was stirred for 1 h a −75° C. Then, a solution of 3-methylquinoline-2-carbaldehyde (1 g, 5.84 mmol) in 20 mL of THF was added. The reaction mixture was stirred for 5 h at −75° C. and then allowed to warm up to room temperature overnight. For work-up, the reaction mixture was diluted with diisopropyl ether (1:1) and the precipitate formed was sucked off. The filtrate was concentrated and triturated in diisopropyl ether. The precipitate was sucked off. The filtrate was purified by column chromatography (normal phase, eluent: cyclohexane/EA) to give 492.5 mg (34%) of the title compound as yellow solid. LC-MS: m/e 248.0 (M+H)+; Rt 1.561 min.

1. additionwas added portionwise at −75° C. under argon
2. additionAfter completion of the addition
3. stirringThe reaction mixture was stirred for 5 h at −75° C.
4. temperatureto warm up to room temperature overnight
5. customthe precipitate formed
6. concentrationThe filtrate was concentrated
7. customtriturated in diisopropyl ether
8. customThe filtrate was purified by column chromatography (normal phase, eluent: cyclohexane/EA)