1,4-Cyclohexanedione → 4-Benzylidenecyclohexanone

HRID 67689

반응식

HRID 67689 반응식
[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

참가 물질

6

반응물 3

HCID 125111,4-CyclohexanedioneHCID 2734970Benzyltriphenylphosphonium bromideHCID 178418339Butyllithium

생성물 1

HCID 197051964-Benzylidenecyclohexanone수율 120%

시약·촉매·용매 2

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d5cd9f739af5413aa3c9e451bf0a50a4
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04346101

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