反応 #52640

反応方程式

3-cyclohexyl-4-morpholinoethoxychlorobenzene

Naphthalene

lithium

Dimethylformamide

→

3-cyclohexyl-4-morpholinoethoxybenzaldehyde

収率 38.3%

溶媒

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他(approximately 1 hour)
2. 2
   温度the reaction was warmed to 0° C.
3. 3
   workup.STIRRINGstirred for an additional hour
4. 4
   workup.STIRRINGthe reaction was stirred at 0° C. for one more hour
5. 5
   温度warmed to room temperature
6. 6
   workup.STIRRINGstirred for another hour
7. 7
   その他The reaction was quenched with methanol (30 ml)
8. 8
   workup.ADDITIONadded to 1N hydrochloric acid (300 ml)
9. 9
   抽出extracted with ethyl acetate (400 ml)
10. 10
    洗浄The organic layer was washed with water (300 ml), saturated sodium bicarbonate solution (300 ml) and brine (300 ml)
11. 11
    乾燥dried over magnesium sulfate
12. 12
    濃縮concentrated

実験手順

Naphthalene (3.48 g, 27.2 mmol) was added to a suspension of 30% lithium dispersion (3.2 g, 138 mmol, pre-washed with tetrahydrofuran) in tetrahydrofuran (80 ml). The suspension was stirred until a green color appeared (approximately 1 hour). The reaction was cooled to −78° C., and a solution of the 3-cyclohexyl-4-morpholinoethoxychlorobenzene (8 g, 24.7 mmol) in tetrahydrofuran (20 ml) was added. After 1 hour, the reaction was warmed to 0° C. and stirred for an additional hour. Dimethylformamide (9.6 ml, 123.5 mmol) was added, the reaction was stirred at 0° C. for one more hour and then warmed to room temperature and stirred for another hour. The reaction was quenched with methanol (30 ml), added to 1N hydrochloric acid (300 ml) and extracted with ethyl acetate (400 ml). The organic layer was washed with water (300 ml), saturated sodium bicarbonate solution (300 ml) and brine (300 ml), dried over magnesium sulfate and concentrated. Chromatography (silica, 40-60% ethyl acetate/hexanes) afforded 3 g (34%) of 3-cyclohexyl-4-morpholinoethoxybenzaldehyde as a light yellow oil.

出典