Acetylene → 1-Chloro-6-phthalimidohex-1-en-3-one

HRID 917955

反応式

HRID 917955 の反応式
[Cl-:1].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:21])[N:9]([CH2:10][CH2:11][CH2:12][C:13](Cl)=[O:14])[C:8](=[O:16])[C:7]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:6]12.[CH:22]#[CH:23]>ClC(Cl)C(Cl)Cl>[Cl:1][CH:22]=[CH:23][C:13](=[O:14])[CH2:12][CH2:11][CH2:10][N:9]1[C:8](=[O:16])[C:7]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:6]2[C:5]1=[O:21]

参加物

5

反応物 3

HCID 6326AcetyleneHCID 5948864-(1,3-Dioxoisoindolin-2-yl)butanoyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 537373061-Chloro-6-phthalimidohex-1-en-3-one

試薬・触媒・溶媒 1

HCID 65911,1,2,2-Tetrachloroethane溶媒

実験手順

Aluminum chloride (43 g) is added to a stirred solution of 4-phthalimidobutyryl chloride (36.2 g) in 1,1,2,2-tetrachloroethane (400 ml), previously saturated with acetylene. Acetylene is bubbled through the solution overnight, with stirring, and the reaction mixture is then decomposed by the addition of crushed ice (300 g). The organic layer is separated and the aqueous layer extracted with 1,1,2,2-tetrachloroethane (3 × 100 ml). The combined organic solution is dried over sodium sulphate and concentrated. The residual solid is recrystallized from hexane affording 1-chloro-6-phthalimidohex-1-en-3-one, m.p. 92°C.

後処理

  1. customAcetylene is bubbled through the solution overnight
  2. additionthe reaction mixture is then decomposed by the addition of crushed ice (300 g)
  3. customThe organic layer is separated
  4. extractionthe aqueous layer extracted with 1,1,2,2-tetrachloroethane (3 × 100 ml)
  5. dry with materialThe combined organic solution is dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residual solid is recrystallized from hexane

出典と根拠

ORDレコード
ord-4080ad020c2844d3aae0d54dfe32d5fc
出典データセット
uspto-grants-1976_07
特許番号
US03968216

関連ノート

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