Dimethyl 5-(1-hydroxy-2-nitroethyl)isophthalate → Dimethyl 5-(2-nitrovinyl)isophthalate

HRID 587937ノート

反応式

HRID 587937 の反応式
O[CH:2]([C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])[CH2:3][N+:4]([O-:6])=[O:5]>C(Cl)Cl.C(OC(=O)C)(=O)C.CN(C)C1C=CN=CC=1>[N+:4]([CH:3]=[CH:2][C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])([O-:6])=[O:5]

参加物

5

反応物 1

HCID 68474723Dimethyl 5-(1-hydroxy-2-nitroethyl)isophthalate

生成物 1

HCID 68478188Dimethyl 5-(2-nitrovinyl)isophthalate

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 7918Acetic Anhydride溶媒

反応条件

温度
22 °C

実験手順

To a solution of 2.29 g (8.09 mmol) of dimethyl 5-(1-hydroxy-2-nitroethyl)isophthalate in 50 mL of DCM and 10 mL of acetic anhydride at 22° C. was added 100 mg of 4-dimethylaminopyridine. The solution was stirred at 22° C. for 1.5 h, evaporated and then coevaporated with xylenes (the material darkened slightly). The residue was partitioned between 100 mL of DCM and 50 mL of 1 N HCl. The organic layer was washed with water (50 mL), satd NaHCO3, dried (Na2SO4) and evaporated. The resulting residue was purified by flash chromatography on silica gel eluting with DCM to give dimethyl 5-(2-nitrovinyl)isophthalate as a light yellow solid.

後処理

  1. customevaporated
  2. customThe residue was partitioned between 100 mL of DCM and 50 mL of 1 N HCl
  3. washThe organic layer was washed with water (50 mL), satd NaHCO3
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe resulting residue was purified by flash chromatography on silica gel eluting with DCM

出典と根拠

ORDレコード
ord-779c57fb7faa4cbc952e9c7e62459a33
出典データセット
uspto-grants-2016_01
特許番号
US09227918B2

反応ノート

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