Реакция #554152

Уравнение реакции

Oxalyl chloride

2-(carboxy)(phenyl)methylthio-3-(4-methylphenyl)propionate

tetrahydrofuran

→

methyl trans-7-methyl-5-oxo-4-phenyl-1,2,4,5-tetrahydro-3-benzothiepine-2-carboxylate

Выход 30.0%

Условия реакции

Обработка

1. 1
   Концентрированиеconcentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residual oil was dissolved in dichloromethane (50 ml)
3. 3
   workup.ADDITIONThe solution was added dropwise to a suspension of aluminum chloride (AlCl3)(21.7 g) and dichloromethane (200 ml) with ice-
4. 4
   Температураcooling
5. 5
   workup.STIRRINGThe reaction mixture was stirred for 2 hours with ice-
6. 6
   Температураcooling
7. 7
   workup.ADDITIONpoured into ice-water
8. 8
   ДругоеThe dichloromethane layer was separated
9. 9
   Промывкаwashed with water
10. 10
    Сушкаdried (MgSO4)
11. 11
    workup.DISTILLATIONdistilled off

Методика

Oxalyl chloride (11.3 g) and DMF (3 drops) were successively added dropwise to a solution of 2-(carboxy)(phenyl)methylthio-3-(4-methylphenyl)propionate (25.5 g) in tetrahydrofuran (THF) (150 ml), followed by stirring for 1.5 hours at room temperature and concentrated under reduced pressure. The residual oil was dissolved in dichloromethane (50 ml). The solution was added dropwise to a suspension of aluminum chloride (AlCl3)(21.7 g) and dichloromethane (200 ml) with ice-cooling. The reaction mixture was stirred for 2 hours with ice-cooling and poured into ice-water. The dichloromethane layer was separated, washed with water, dried (MgSO4) and distilled off to give crystals of methyl trans-7-methyl-5-oxo-4-phenyl-1,2,4,5-tetrahydro-3-benzothiepine-2-carboxylate (7.2 g, 30%). Recrystallization from ethyl acetate-hexane gave colorless prisms.

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