1,4-Cyclohexanedione → 4-Benzylidenecyclohexanone

HRID 67689

反応式

HRID 67689 の反応式
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Li])CCC.[C:33]1(=O)[CH2:38][CH2:37][C:36](=[O:39])[CH2:35][CH2:34]1>C1COCC1.CCCCC>[CH:2](=[C:33]1[CH2:34][CH2:35][C:36](=[O:39])[CH2:37][CH2:38]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 125111,4-CyclohexanedioneHCID 2734970Benzyltriphenylphosphonium bromideHCID 178418339Butyllithium

生成物 1

HCID 197051964-Benzylidenecyclohexanone収率 120%

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mechanically stirred suspension of 15.24 g (0.035 mole) of benzyltriphenylphosphonium bromide in 150 ml of THF there was added first 22 ml of 1.61 N n-butyllithium in pentane and then 5.0 g (0.032 mole) of cyclohexane-1,4-dione, ethylene monoketal in 50 ml of THF. Following 5 hours' heating at reflux the mixture was allowed to cool and was then washed in turn with water and brine. The organic layer was concentrated, and the residue was chromatographed on 1 liter of silica gel, eluting with 20% ethyl acetate in Skellysolve® B, to afford 7.15 g (97%) of 4-benzylidenecyclohexanone, ethylene ketal as an oil, the nmr spectrum of which is in consonance with the structure.

後処理

  1. temperature' heating
  2. temperatureat reflux the mixture
  3. temperatureto cool
  4. washwas then washed in turn with water and brine
  5. concentrationThe organic layer was concentrated
  6. customthe residue was chromatographed on 1 liter of silica gel
  7. washeluting with 20% ethyl acetate in Skellysolve® B

出典と根拠

ORDレコード
ord-d5cd9f739af5413aa3c9e451bf0a50a4
出典データセット
uspto-grants-1982_08
特許番号
US04346101

関連ノート

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