反应 #582502

ord-0dc7a94483894b17b716ed6beacbeb41

反应方程式

O=Cc1ccc(OC2CCCCO2)cc1
1CW01
O=Cc1ccc(OC2CCCCO2)cc1
4-(Tetrahydro-pyran-2-yloxy)-benzaldehyde
[Na+].[OH-]
NaOH
O=C1CCCC1
Cyclopentanone
O=Cc1ccccc1
benzaldehyde
O=C1C(=Cc2ccc(OC3CCCCO3)cc2)CCC1=Cc1ccc(OC2CCCCO2)cc1
solid
收率 74.0%
O=C1C(=Cc2ccc(OC3CCCCO3)cc2)CCC1=Cc1ccc(OC2CCCCO2)cc1
2,5-Bis-[4-(tetrahydro-pyran-2-yloxy)-benzylidene]-cyclopentanone
收率 74.0%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.ADDITIONThis was then added to the THP
  2. 2
    workup.WAITthe mixture was left
  3. 3
    workup.STIRRINGto stir at room temperature for approximately 16 hours
  4. 4
    其他A solid precipitate was isolated by vacuum filtration
  5. 5
    洗涤washed with water (2×50 ml)
  6. 6
    其他This solid was recrystallised from ethanol

实验过程

Cyclopentanone (8.8 ml, 0.099 mol) was dissolved in ethanol (12 ml) and added to NaOH dissolved in water (25 ml) and ethanol (7 ml), and was left to stir for 25 min. This was then added to the THP protected benzaldehyde from 1CW01 (46.12 g, 0.22 mol), and the mixture was left to stir at room temperature for approximately 16 hours. A solid precipitate was isolated by vacuum filtration, washed with water (2×50 ml) and then ethanol (4×40 ml). This solid was recrystallised from ethanol to give a yellow solid (33.74 g, 74%).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US06939479B2uspto-grants-2005_09