Hydrochloric Acid → 3-Ethyl-6-(methyloxy)-2-phenyl-3,4-dihydro-1(2H)-naphthalenone

HRID 1992850Notes

Reaction equation

HRID 1992850 reaction equation
COC1C=[C:5]([CH2:9][CH:10]([CH2:21][CH3:22])[CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([OH:14])=O)[CH:6]=[CH:7][CH:8]=1.[C:23](Cl)(=[O:27])[C:24](Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].Cl.[CH2:34](Cl)Cl>CN(C=O)C>[CH2:21]([CH:10]1[CH2:9][C:5]2[C:6](=[CH:7][CH:8]=[C:23]([O:27][CH3:34])[CH:24]=2)[C:12](=[O:14])[CH:11]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH3:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 685374623-{[3-(Methyloxy)phenyl]methyl}-2-phenylpentanoic acid

Product 1

HCID 685413613-Ethyl-6-(methyloxy)-2-phenyl-3,4-dihydro-1(2H)-naphthalenoneYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To a solution of 3-{[3-(methyloxy)phenyl]methyl}-2-phenylpentanoic acid (54) (0.98 g, 3.28 mmol) in CH2Cl2 (20 mL) at room temperature was added oxalyl chloride (0.88 mL, 9.85 mmol) followed by one drop of DMF. The mixture was stirred at room temperature overnight. CH2Cl2 and excess of oxalyl chloride were removed under vacuum. The residue was dissolved in CH2Cl2 (30 mL), cooled in an ice bath, AlCl3 (0.67 g, 4.93 mmol) was added. The resulting brown solution was stirred at 0° C. for 5 h. Poured into 1 N HCl (35 mL) with ice, and the mixture was extracted with CH2Cl2. The extracts were combined and washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a yellow oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (6.5:1) to give 0.84 g (91%) of the title compound (55) as a greenish-yellow oil. 1HNMR indicated it was a mixture of two diastereomers with a ratio of 2:1.

Workup

  1. customCH2Cl2 and excess of oxalyl chloride were removed under vacuum
  2. dissolutionThe residue was dissolved in CH2Cl2 (30 mL)
  3. temperaturecooled in an ice bath
  4. stirringThe resulting brown solution was stirred at 0° C. for 5 h
  5. extractionthe mixture was extracted with CH2Cl2
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customto give the crude product as a yellow oil
  11. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (6.5:1)

Sources & evidence

ORD record
ord-51f8098d311f46e5aa61b71f0901496e
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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