Pyridine → (5-Oxocyclopent-1-en-1-yl)acetaldehyde
Reaction equation
N1C=CC=CC=1.[OH:7][CH2:8][CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1>[O-2].[O-2].[O-2].[Cr+6].C(Cl)Cl>[CH:8]([CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1)=[O:7]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Chromium trioxide (0.6 mol) is added to a stirring solution of (1.2 mol) of anhydrous pyridine in 1500 ml. of anhydrous methylene chloride cooled in an ice bath. The deep red suspension is stirred for 15 minutes at 0° C. and 45 minutes at ambient temperature. A solution of 01.5 mol of 2-(2-hydroxyethyl)-cyclopent-2-en-1-one (Example 897) in 50 ml. of methylene chloride is added, all at once, to the suspension. A black terry deposit is formed immediately. After stirring the mixture for 25 minutes at ambient temperature, the methylene chloride is decanted from the tarry precipitate which is then triturated several times with ether.
Workup
- customA black terry deposit is formed immediately
- stirringAfter stirring the mixture for 25 minutes at ambient temperature
- customthe methylene chloride is decanted from the tarry precipitate which
- customis then triturated several times with ether
Sources & evidence
- ORD record
- ord-7658afd9dda34173acee7217b0c1a190
- Source dataset
- uspto-grants-1977_11
- Patent number
- US04060540
Reaction notes
Loading…