反応 #2460295

反応方程式

Methanol

2-[(3-methoxyphenyl)thio]diethylbenzamide

lithium diisopropylamide

→

1-methoxythioxanthen-9-one

溶媒

tetrahydrofuran

tetrahydrofuran

heptane THF

反応条件

後処理

1. 1
   温度The reaction mixture was warmed to ambient and
2. 2
   洗浄the resulting solution was washed twice with water
3. 3
   乾燥The solution was dried (Na2SO4)
4. 4
   その他the solvent was removed at reduced pressure
5. 5
   その他This crude product was recrystallized from methanol
6. 6
   その他to provide 0.15 g (45% of theory) of a yellow solid

実験手順

Finally, 1-methoxythioxanthen-9-one (S-12) was prepared. A stirred mixture of 2.05 mL of a 2.0 M solution in heptane/THF of lithium diisopropylamide (4.1 mmol) diluted with 15 mL of anhydrous tetrahydrofuran was cooled to 0° C. and treated dropwise with a solution of 2-[(3-methoxyphenyl)thio]diethylbenzamide (0.4 g, 1.4 mmol) in 3 mL of anhydrous tetrahydrofuran. The reaction mixture was warmed to ambient and stirred for 2 h. Methanol (1 mL) was added, and the resulting solution was washed twice with water, and then with brine. The solution was dried (Na2SO4) and the solvent was removed at reduced pressure to deposit a yellow solid. This crude product was recrystallized from methanol to provide 0.15 g (45% of theory) of a yellow solid. 1H NMR (CDCl3): δ 4.00 (s, 3H), 7.92 (d, 1H), 7.12 (d, 1H), 7.50 (m, 4H), 8.45 (d, 1H).

出典