Benzaldehyde → 2-Benzyloxystilbene

HRID 743406

반응식

HRID 743406 반응식
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[CH2:10]([O:17][C:18]1[CH:43]=[CH:42][CH:41]=[CH:40][C:19]=1[CH2:20][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N12CCCN=C1CCCCC2>C(#N)C>[CH2:10]([O:17][C:18]1[CH:43]=[CH:42][CH:41]=[CH:40][C:19]=1[CH:20]=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 240BenzaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 194239672-Benzyloxybenzyltriphenylphosphonium chloride

생성물 1

HCID 544184572-Benzyloxystilbene수율 76%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

5.09 g of benzaldehyde and 26.1 g of 2-benzyloxybenzyltriphenylphosphonium chloride (prepared as described in Preparation 1) were dissolved in 100 ml of acetonitrile, with heating. 8.04 g of 1,8-diazabicyclo[5.4.0]undec-7-ene were then added dropwise to the solution at 80° C., whilst stirring, and the resulting mixture was stirred at the same temperature for 40 minutes. 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 concentrated by distillation under reduced pressure, and 100 ml of a 2:1 by volume mixture of hexane and ethyl acetate were added to the resulting residue, and the mixture was agitated. Insoluble materials were filtered off, and the filtrate was concentrated by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 30:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 10.4 g (yield 76%) of 2-benzyloxystilbene.

후처리

  1. temperaturewith heating
  2. stirringthe resulting mixture was stirred at the same temperature for 40 minutes
  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. concentrationThe organic layer was concentrated by distillation under reduced pressure, and 100 ml of a 2:1 by volume mixture of hexane and ethyl acetate
  6. additionwere added to the resulting residue
  7. stirringthe mixture was agitated
  8. filtrationInsoluble materials were filtered off
  9. concentrationthe filtrate was concentrated by distillation under reduced pressure
  10. customThe resulting residue was purified by column chromatography through silica gel
  11. additionby volume mixture of hexane and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-6e330f2d289f41879443a2ac1edbe8bd
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556864

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