Potassium Cyanide → 5-(4-Fluorobenzoyl)-6-cyano-2-methylsulfonylnaphthalene

HRID 1858008ノート

反応式

HRID 1858008 の反応式
[F:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([C:8]2[C:17](OS(C(F)(F)F)(=O)=O)=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:13]3)=[O:7])=[CH:4][CH:3]=1.[C-:32]#[N:33].[K+]>O1CCOCC1.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:17]([C:32]#[N:33])=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][C:12]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:13]3)=[O:7])=[CH:30][CH:31]=1

参加物

6

反応物 2

HCID 9032Potassium CyanideHCID 221256945-(4-Fluorobenzoyl)-6-trifluoromethylsulfonyloxy-2-methylsulfonylnaphthalene

生成物 1

HCID 99284855-(4-Fluorobenzoyl)-6-cyano-2-methylsulfonylnaphthalene収率 63.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

A mixture of 5-(4-fluorobenzoyl)-6-trifluoromethylsulfonyloxy-2-methylsulfonylnaphthalene (2.5 g, 5.2 mmol) [prepared as described in step 1 above], potassium cyanide (0.41 g, 6.3 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.30 g, 0.26 mmol) in dioxane (50 ml) was heated at reflux under argon. After 16 h, the reaction mixture was cooled to RT, poured into brine, and the product wias extracted into ethyl acetate. The organic layer was dried with sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography (gradient elution, 10-60% ethyl acetate/hexane) and then recrystallized from ethyl acetate-hexane to give 1.16 g of 5-(4-fluorobenzoyl)-6-cyano-2-methylsulfonylnaphthalene as a solid (63% yield).

後処理

  1. temperaturewas heated
  2. temperatureat reflux under argon
  3. extractionthe product wias extracted into ethyl acetate
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography (gradient elution, 10-60% ethyl acetate/hexane)
  7. customrecrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-3ced89916d9e48139bb5831275ff9a2d
出典データセット
uspto-grants-2000_11
特許番号
US06150397

反応ノート

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