Реакция #77987

Уравнение реакции

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

t-butyl 3-acetoxy-4-nitrophenylacetate

methyl magnesium chloride

methyl magnesium chloride

→

title compound

t-Butyl 3-acetoxy-5-methyl-4-nitrophenylacetate

Растворители

tetrahydrofuran

diethyl ether

diethyl ether

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred at room temperature overnight
2. 2
   Другоеpartially evaporated
3. 3
   workup.ADDITIONtreated with dichloromethane
4. 4
   ПромывкаThe mixture was washed with water
5. 5
   Другоеdried
6. 6
   Другоеevaporated

Методика

A stirred solution of t-butyl 3-acetoxy-4-nitrophenylacetate (8.0 g, Reference Example 13) in tetrahydrofuran (350 mL) at −15° C. under argon was treated dropwise with methyl magnesium chloride solution in diethyl ether (7mL, 3M) and after 2 hours a further aliquot of methyl magnesium chloride solution in diethyl ether (7 mL, 3M). After stirring for a further 1 hour the reaction mixture was treated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (10.4 g), then stirred at room temperature overnight, then partially evaporated and then treated with dichloromethane. The mixture was washed with water, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with dichloromethane to give the title compound (1.66 g) as a yellow oil.

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