6-Nitroveratraldehyde → HCID 178487640、化合物

HRID 251798ノート

反応式

HRID 251798 の反応式
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1.[F-].[K+].C1([S:24][CH:25]([N:30]=[C:31]=S)[Si](C)(C)C)C=CC=CC=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][C:6]([C:7]2[O:8][C:25]([SH:24])=[N:30][CH:31]=2)=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1

参加物

6

反応物 3

HCID 885056-NitroveratraldehydeHCID 522689Potassium FluorideHCID 13240488Phenylthio(trimethylsilyl)methyl isothiocyanate

生成物 1

HCID 178487640HCID 178487640、化合物収率 18%

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 6342Acetonitrile溶媒

実験手順

4,5-Dimethoxy-2-nitrobenzaldehyde (1.52 g, 7.19 mmol), 353.0 mg (6.07 mmol) of potassium fluoride, and 134.8 mg (0.59 mmol) of benzyltriethylammonium chloride were added to a solution of 1.51 g (5.97 mmol) of phenylthio(trimethylsilyl)methyl isothiocyanate, synthesized according to a document (J. Chem. Soc., Perkin Trans 1 1984, 435.), in acetonitrile (36 ml), and the mixture was stirred at room temperature overnight. The solvent was removed from the reaction solution by distillation, and the water and chloroform were then added to the residue. The aqueous layer was extracted with chloroform. The organic layer was washed with saturated brine and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1→1:1) to give 302.4 mg (yield 18%) of the title compound.

後処理

  1. customsynthesized
  2. customThe solvent was removed from the reaction solution by distillation
  3. additionthe water and chloroform were then added to the residue
  4. extractionThe aqueous layer was extracted with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas then dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation
  8. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1→1:1)

出典と根拠

ORDレコード
ord-28be155f82dd4f2bb9d6b853b28f3c64
出典データセット
uspto-grants-2011_01
特許番号
US07867980B2

反応ノート

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