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

HRID 50363

反応式

HRID 50363 の反応式
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]

参加物

6

反応物 2

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

生成物 1

HCID 3457222Methyl 4-formyl-3-nitrobenzoate

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f6d982671ef64b3e8ae0bbc2d85e2e0b
出典データセット
uspto-grants-2004_03
特許番号
US06710055B2

関連ノート

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