Methyl 4-dimethylaminovinyl-3-nitrobenzoate → Methyl 4-formyl-3-nitrobenzoate

HRID 50363

반응식

HRID 50363 반응식
CN(C)C=[CH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16].I([O-])(=O)(=O)=[O:20].[Na+]>O1CCCC1.O.O.C(Cl)Cl>[CH:4]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])=[O:20]

참가 물질

6

반응물 2

HCID 894336Methyl 4-dimethylaminovinyl-3-nitrobenzoateHCID 23667635Sodium periodate

생성물 1

HCID 3457222Methyl 4-formyl-3-nitrobenzoate

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

1.2 g (4.8 mmol) of methyl 4-(2-dimethylaminovinyl)-3-nitrobenzoate were dissolved in 120 mL of tetrahydrofuran/water (1:1) and after the addition of 3.0 g (14.3 mmol) of sodium metaperiodate the mixture was stirred for 20 hours at ambient temperature. The suspension was then diluted with water and methylene chloride and extracted with methylene chloride. The combined organic extracts were washed with sodium hydrogen carbonate solution, dried, and evaporated down. The residue was chromatographed on silica gel and eluted with ethyl acetate/cyclohexane (1:3). Yield: 0.6 g (63% of theory); Rf value: 0.63 (silica gel, ethyl acetate/cyclohexane=1:1).

후처리

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts were washed with sodium hydrogen carbonate solution
  3. customdried
  4. customevaporated down
  5. customThe residue was chromatographed on silica gel
  6. washeluted with ethyl acetate/cyclohexane (1:3)

출처 및 근거

ORD 기록
ord-f6d982671ef64b3e8ae0bbc2d85e2e0b
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710055B2

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