Reaction #2460295

Reaction equation

Methanol

2-[(3-methoxyphenyl)thio]diethylbenzamide

lithium diisopropylamide

→

1-methoxythioxanthen-9-one

Solvents

tetrahydrofuran

tetrahydrofuran

heptane THF

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was warmed to ambient and
2. 2
   Washthe resulting solution was washed twice with water
3. 3
   DryingThe solution was dried (Na2SO4)
4. 4
   Otherthe solvent was removed at reduced pressure
5. 5
   OtherThis crude product was recrystallized from methanol
6. 6
   Otherto provide 0.15 g (45% of theory) of a yellow solid

Procedure

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