تفاعل #582502

ord-0dc7a94483894b17b716ed6beacbeb41

معادلة التفاعل

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
المردود 74.0%
O=C1C(=Cc2ccc(OC3CCCCO3)cc2)CCC1=Cc1ccc(OC2CCCCO2)cc1
2,5-Bis-[4-(tetrahydro-pyran-2-yloxy)-benzylidene]-cyclopentanone
المردود 74.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  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
    أخرىA solid precipitate was isolated by vacuum filtration
  5. 5
    غسيلwashed with water (2×50 ml)
  6. 6
    أخرىThis solid was recrystallised from ethanol

الإجراء التجريبي

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%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US06939479B2uspto-grants-2005_09