Dimethylformamide → 3-(1-Phenylvinyl)benzaldehyde

HRID 2422255

反応式

HRID 2422255 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH2:9])[CH:3]=1.C([Li])CCC.CCCCCC.CN(C)[CH:29]=[O:30].[Cl-].[NH4+]>O1CCCC1>[C:10]1([C:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[CH:29]=[O:30])=[CH2:9])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 230831781-Bromo-3-(1-phenylethenyl)benzeneHCID 178418244HCID 178418244、化合物

生成物 1

HCID 131027463-(1-Phenylvinyl)benzaldehyde収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1-bromo-3-(1-phenylvinyl)benzene (1.00 g, 3.86 mmol) in tetrahydrofuran (5 mL) was stirred under a nitrogen atmosphere at −78° C., and 1.6 M n-butyllithium/hexane solution (3 mL, 4.8 mmol) was added dropwise. After 1 hr, N,N-dimethylformamide (0.372 mL, 4.80 mmol) was added, and the mixture was further stirred at the same temperature for 2 hrs. Aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane) to give the title compound (0.626 g, yield 78%) as a colorless oil.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-941befe5b50a4bd3a22e0dda6c60842f
出典データセット
uspto-grants-2011_06
特許番号
US07960369B2

関連ノート

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