Réaction #2460295

Équation de réaction

Methanol

2-[(3-methoxyphenyl)thio]diethylbenzamide

lithium diisopropylamide

→

1-methoxythioxanthen-9-one

Solvants

tetrahydrofuran

tetrahydrofuran

heptane THF

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was warmed to ambient and
2. 2
   Lavagethe resulting solution was washed twice with water
3. 3
   SéchageThe solution was dried (Na2SO4)
4. 4
   Autrethe solvent was removed at reduced pressure
5. 5
   AutreThis crude product was recrystallized from methanol
6. 6
   Autreto provide 0.15 g (45% of theory) of a yellow solid

Mode opératoire

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).

Source