Реакция #65999

Уравнение реакции

methyl (R)-7-(4-fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoate

dichloromethyl methyl ether

→

methyl (R)-7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoate

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Температураwhile maintaining the temperatures of the reaction mixture at a range from -10 ° C. to -12° C
2. 2
   Экстракцияwas subjected to extraction with ethyl acetate
3. 3
   ПромывкаThe organic layer was washed with water
4. 4
   Сушкаby drying over magnesium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
6. 6
   ДругоеThe residue was recrystallized from chloroform/hexane

Методика

To a solution of methyl (R)-7-(4-fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoate (0.8 g, 2.1 mmol) and dichloromethyl methyl ether (0.62 ml) in dichloromethane (10 ml) was added dropwise a solution of titanium tetrachloride (0.76 ml) in dichloromethane (3 ml) under argon atmosphere while maintaining the temperatures of the reaction mixture at a range from -10 ° C. to -12° C. The reaction mixture was then stirred for 30 minutes at the same temperature range. The reaction mixture was then added to ice-water, which was subjected to extraction with ethyl acetate. The organic layer was washed with water, an aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous saline solution, successively, followed by drying over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was recrystallized from chloroform/hexane to afford 0.63 g of methyl (R)-7-(4-fluorophenyl)-7-(3-formyl-6-hydroxy-2,4,5-trimethylphenyl)heptanoate. Physico-chemical properties and spectral data of the product were shown in [Table 4].

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