3-Phenylprop-2-Enal → 1-(2-Benzyloxyphenyl)-4-phenylbutadiene

HRID 743382노트

반응식

HRID 743382 반응식
[CH:1](=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl-].[CH2:12]([O:19][C:20]1[CH:45]=[CH:44][CH:43]=[CH:42][C:21]=1[CH2:22][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N12CCCN=C1CCCCC2.CCCCCC>C(#N)C.C(OCC)(=O)C>[CH2:12]([O:19][C:20]1[CH:45]=[CH:44][CH:43]=[CH:42][C:21]=1[CH:22]=[CH:1][CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

7

반응물 4

HCID 3073-Phenylprop-2-EnalHCID 8058HexaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 194239672-Benzyloxybenzyltriphenylphosphonium chloride

생성물 1

HCID 545219991-(2-Benzyloxyphenyl)-4-phenylbutadiene수율 97.7%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

5.28 g of cinnamaldehyde and 19.8 g of 2-benzyloxybenzyltriphenylphosphonium chloride (prepared as described in Preparation 1) were dissolved, with heating, in 200 ml of acetonitrile, and then 6 g of 1,8-diazabicyclo[5,4,0]undec-7-ene were added dropwise to the solution. The resulting mixture was then heated under reflux for 3 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was partitioned between ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The oily residue thus obtained was again dissolved in 200 ml of ethyl acetate, with heating, and 50 ml of hexane was added to the solution, after which deposited insoluble materials were filtered off. The filtrate was concentrated by evaporation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 9:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 12.2 g (yield 97.7%) of 1-(2-benzyloxyphenyl)-4-phenylbutadiene as a colorless oil.

후처리

  1. temperatureThe resulting mixture was then heated
  2. temperatureunder reflux for 3 hours
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. customthe resulting residue was partitioned between ethyl acetate and water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe oily residue thus obtained
  8. temperaturewith heating
  9. filtrationwere filtered off
  10. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  11. customthe resulting residue was purified by column chromatography through silica gel
  12. additionby volume mixture of hexane and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-4f78d7c5fd1e4f549e2b1a3af35eac68
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556864

반응 노트

불러오는 중…