4-Toluenesulfonyl chloride → 2-Cyano-1-(2-furyl)vinyl 4-methylbenzenesulfonate

HRID 1786929ノート

反応式

HRID 1786929 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:10])[CH2:7][C:8]#[N:9].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[CH3:21][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:10][C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:7][C:8]#[N:9])(=[O:19])=[O:18])=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1416712-Furoylacetonitrile

生成物 1

HCID 545345202-Cyano-1-(2-furyl)vinyl 4-methylbenzenesulfonate収率 92.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a mixture of 3-(2-furyl)-3-oxopropanenitrile (5.29 g), p-toluenesulfonyl chloride (9.00 g) and dichloromethane (60 mL) was added dropwise triethylamine (5.99 g) under ice-cooling. After stirring under ice-cooling for 1.5 hrs, the mixture was diluted with dichloromethane (100 mL). The mixture washed with water (150 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:methyl acetate=9:1→3:1) to give the title compound (10.48 g) as a mixture of (E)-form and (Z)-form (3:1).

後処理

  1. temperaturecooling
  2. temperaturecooling for 1.5 hrs
  3. washThe mixture washed with water (150 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent, hexane:methyl acetate=9:1→3:1)

出典と根拠

ORDレコード
ord-b8cb0c29e4c24630a8584314d898a303
出典データセット
uspto-grants-2009_03
特許番号
US07507740B2

反応ノート

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