Oxalyl chloride → 2-[6-(Chloroformyl)hexyl]cyclopent-2-en-1-one

HRID 426621Notes

Reaction equation

HRID 426621 reaction equation
[Na].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:12](=[O:16])[CH2:13][CH2:14][CH:15]=1)(O)=[O:3].C(Cl)(=O)C([Cl:20])=O>O1CCCC1.CCOCC>[Cl:20][C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[C:12](=[O:16])[CH2:13][CH2:14][CH:15]=1)=[O:3]

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 789025-Oxo-1-cyclopentene-1-heptanoic acidHCID 5360545Sodium

Product 1

HCID 202875962-[6-(Chloroformyl)hexyl]cyclopent-2-en-1-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 1.94 g (0.08 mol) of sodium hydri in 100 ml of tetrahydrofuran is added with stirring under argo dropwise a solution of 17 g (0.08 mol) of 2-(6-carboxyhexyl)-cyclopent-2-en-1-one in 160 ml of tetrahydrofuran. After the addition is complete, the mixture is stirred for 1 hour 15 minutes. The mixture is cooled to 0° C. and 13 ml of oxalyl chloride is added. The mixture is stirred at 0° C. for 30 minutes and at room temperature for 30 minutes. The solution is diluted with 500 ml of ether and filtered through Celite. The solvent is removed from the filtrate and the residue is extracted with hot hexane twice. The hexane is removed to give 16.0 g of the title compound.

Workup

  1. additionis added
  2. additionAfter the addition
  3. stirringThe mixture is stirred at 0° C. for 30 minutes and at room temperature for 30 minutes
  4. filtrationfiltered through Celite
  5. customThe solvent is removed from the filtrate
  6. extractionthe residue is extracted with hot hexane twice
  7. customThe hexane is removed

Sources & evidence

ORD record
ord-b591b60051dc4b9fae5e574a50a6c78b
Source dataset
uspto-grants-1979_10
Patent number
US04170597

Reaction notes

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