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

HRID 587937노트

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HRID 587937 반응식
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]

참가 물질

5

반응물 1

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

생성물 1

HCID 68478188Dimethyl 5-(2-nitrovinyl)isophthalate

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 7918Acetic Anhydride용매

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온도
22 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-779c57fb7faa4cbc952e9c7e62459a33
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227918B2

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