Реакция #2460295

Уравнение реакции

Methanol

2-[(3-methoxyphenyl)thio]diethylbenzamide

lithium diisopropylamide

→

1-methoxythioxanthen-9-one

Растворители

tetrahydrofuran

tetrahydrofuran

heptane THF

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was warmed to ambient and
2. 2
   Промывкаthe resulting solution was washed twice with water
3. 3
   СушкаThe solution was dried (Na2SO4)
4. 4
   Другоеthe solvent was removed at reduced pressure
5. 5
   ДругоеThis crude product was recrystallized from methanol
6. 6
   Другоеto provide 0.15 g (45% of theory) of a yellow solid

Методика

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).

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