Pyridine → (5-Oxocyclopent-1-en-1-yl)acetaldehyde

HRID 67003Notes

Reaction equation

HRID 67003 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

HCID 1049PyridineHCID 154144942-(2-Hydroxyethyl)cyclopent-2-en-1-one

Product 1

HCID 20465672(5-Oxocyclopent-1-en-1-yl)acetaldehyde

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

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

  1. customA black terry deposit is formed immediately
  2. stirringAfter stirring the mixture for 25 minutes at ambient temperature
  3. customthe methylene chloride is decanted from the tarry precipitate which
  4. customis then triturated several times with ether

Sources & evidence

ORD record
ord-1e6f811340d64e7ab1cee8122f6e7906
Source dataset
uspto-grants-1982_08
Patent number
US04343949

Reaction notes

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