Reacción #2460295

Ecuación de reacción

Methanol

2-[(3-methoxyphenyl)thio]diethylbenzamide

lithium diisopropylamide

→

1-methoxythioxanthen-9-one

Disolventes

tetrahydrofuran

tetrahydrofuran

heptane THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was warmed to ambient and
2. 2
   Lavadothe resulting solution was washed twice with water
3. 3
   SecadoThe solution was dried (Na2SO4)
4. 4
   Otrothe solvent was removed at reduced pressure
5. 5
   OtroThis crude product was recrystallized from methanol
6. 6
   Otroto provide 0.15 g (45% of theory) of a yellow solid

Procedimiento

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).

Fuente