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

HRID 49709ノート

反応式

HRID 49709 の反応式
[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]

参加物

6

反応物 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 18188103t-Butyl 3-acetoxy-4-nitrophenylacetateHCID 178418332HCID 178418332、化合物2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-acffe975056b4b4b987c21ee70571b50
出典データセット
uspto-grants-2004_03
特許番号
US06706738B2

反応ノート

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