반응 #2460295

반응 방정식

Methanol

2-[(3-methoxyphenyl)thio]diethylbenzamide

lithium diisopropylamide

→

1-methoxythioxanthen-9-one

용매

tetrahydrofuran

tetrahydrofuran

heptane THF

반응 조건

후처리

1. 1
   온도The reaction mixture was warmed to ambient and
2. 2
   세척the resulting solution was washed twice with water
3. 3
   건조The solution was dried (Na2SO4)
4. 4
   기타the solvent was removed at reduced pressure
5. 5
   기타This crude product was recrystallized from methanol
6. 6
   기타to provide 0.15 g (45% of theory) of a yellow solid

실험 절차

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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