2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → t-Butyl 3-acetoxy-5-methyl-4-nitrophenylacetate

HRID 1357868노트

반응식

HRID 1357868 반응식
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])(=[O:3])[CH3:2].[CH3:22][Mg]Cl.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCCC1.C(OCC)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:8]=[C:9]([CH3:22])[C:10]=1[N+:11]([O-:13])=[O:12])(=[O:3])[CH3:2]

참가 물질

6

반응물 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18188103t-Butyl 3-acetoxy-4-nitrophenylacetateHCID 178418332HCID 178418332, 화합물2회

생성물 1

HCID 18188096t-Butyl 3-acetoxy-5-methyl-4-nitrophenylacetate

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매

실험 절차

A stirred solution of t-butyl 3-acetoxy-4-nitrophenylacetate (8.0 g, Reference Example 18) in tetrahydrofuran (350 mL) at −15° C. under argon was treated dropwise with methyl magnesium chloride solution in diethyl ether (7 mL, 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.

후처리

  1. stirringstirred at room temperature overnight
  2. custompartially evaporated
  3. additiontreated with dichloromethane
  4. washThe mixture was washed with water
  5. customdried
  6. customevaporated

출처 및 근거

ORD 기록
ord-c71e9d00b83b43c1afcf78da9f6e3af0
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06593354B2

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