Aluminum(III) Chloride → HCID 20297066, compound

HRID 1389566Notes

Reaction equation

HRID 1389566 reaction equation
[C:1]([C:5]1([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][CH2:11][CH2:12]2)=CC1C(C)C([O-])=O)(=[O:4])[CH2:2]C.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[C:1]([C:2]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:13]=2[CH:14]=[C:5]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[C:1]=1[OH:4])(=[O:4])[CH2:5][CH3:14]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 86737436HCID 86737436, compound

Product 1

HCID 20297066HCID 20297066, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

1.45 g of 3-propionyl-3-acetylaminomethyl-5,6,7,8-tetrahydro-2-naphthylpropionate was dissolved in 5 ml of methylene chloride and 2.0 g of aluminum chloride was added to the solution. After a homogeneous solution was formed, methylene chloride was distilled off from the reaction system while raising temperature and solution was heated at 100° C. for 10 minutes. After allowing the solution to cool, water was added thereto, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with water, an aqueous solution bicarbonate solution and an aqueous sodium chloride solution, dried and concentrated. The residue was chromatographed on silica gel column using a mixed solvent of methylene chloride: ethyl acetate (10:1 by volume) to obtain 640 mg of the title compound having the following physical properties.

Workup

  1. customAfter a homogeneous solution was formed
  2. distillationmethylene chloride was distilled off from the reaction system
  3. temperaturewhile raising temperature and solution
  4. temperatureto cool
  5. additionwater was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed successively with water
  8. dry with materialan aqueous solution bicarbonate solution and an aqueous sodium chloride solution, dried
  9. concentrationconcentrated
  10. customThe residue was chromatographed on silica gel column

Sources & evidence

ORD record
ord-f00f4abe1f4d4e159a8abd47d5b9bb64
Source dataset
uspto-grants-1981_01
Patent number
US04245099

Reaction notes

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