Water → 2-Chlorocinnamaldehyde

HRID 537392

反応式

HRID 537392 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[CH2:9]([OH:12])[CH:10]=[CH2:11].C([O-])(O)=O.[Na+].O>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:11]=[CH:10][CH:9]=[O:12]

参加物

8

反応物 4

HCID 962WaterHCID 7858Allyl AlcoholHCID 119931-Chloro-2-iodobenzeneHCID 516892Sodium Bicarbonate

生成物 1

HCID 30140422-Chlorocinnamaldehyde収率 74%

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
30 °C

実験手順

A mixture of 2.2 mL (18 mmol) of 2-chloroiodobenzene, 1.8 mL (27 mmol) of allyl alcohol, 81 mg (0.36 mmol) of Pd(OAc)2, 5.3 g (18 mmol) of Bu4NCl, and 3.8 g (45 mmol) of NaHCO3 in 50 mL of DMF is stirred under Ar2 at 30° C. for 24 h. Water is added and the mixture is extracted with EtOAc. The extract is washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (0-50% EtOAc in hexanes) provides 2.2 g (74%) of 3-(2-chlorophenyl)propenal.

後処理

  1. extractionthe mixture is extracted with EtOAc
  2. washThe extract is washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-6790add3008d4712b95d944557dca659
出典データセット
uspto-grants-2014_10
特許番号
US08859814B2

関連ノート

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