Trichloroacetyl chloride → HCID 90079810, compound

HRID 2276732Notes

Reaction equation

HRID 2276732 reaction equation
[CH2:1]([CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:2]=[CH2:3].P(Cl)(Cl)(Cl)=O.[Cl:20][C:21]([Cl:26])(Cl)[C:22](Cl)=[O:23]>CCOCC.[Cu].[Zn]>[Cl:20][C:21]1([Cl:26])[C:22](=[O:23])[CH2:3][CH:2]1[CH2:1][CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 24813Phosphorus oxychlorideHCID 74900Diethyl allylmalonate

Product 1

HCID 90079810HCID 90079810, compound

Reagents, catalysts & solvents 2

HCID 10290809Zinc copper coupleCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of Cu.Zn (1.771 g, 13.73 mmol) and diethyl 2-allylmalonate (1.084 mL, 5.49 mmol) in anhydrous Et2O (20 mL) at reflux was added a solution of phosphorus oxychloride (1.127 mL, 12.09 mmol) and 2,2,2-trichloroacetyl chloride (1.357 mL, 12.09 mmol) in Et2O (10 mL) dropwise through an addition funnel over 2 h. The resulting mixture was then heated at reflux overnight. After cooling to room temperature, the mixture was filtered through CELITE® and washed with EtOAc. The filtrate was concentrated and the residue was purified by silica gel column chromatography (80 g, EtOAc/hexane=0-50%) to afford Preparation 7A (1.59 g, 93%).

Workup

  1. temperatureat reflux
  2. temperatureThe resulting mixture was then heated
  3. temperatureat reflux overnight
  4. filtrationthe mixture was filtered through CELITE®
  5. washwashed with EtOAc
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography (80 g, EtOAc/hexane=0-50%)
  8. customto afford

Sources & evidence

ORD record
ord-cb57e9b69bdf48f0910b3776b9237018
Source dataset
uspto-grants-2015_09
Patent number
US09133126B2

Reaction notes

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