Hydrochloric Acid → HCID 23169890, compound

HRID 882713Notes

Reaction equation

HRID 882713 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12](O)=[O:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.CN1CCOCC1>O1CCCC1.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH:12]=[O:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 855751-(4-Methoxyphenyl)cyclopropane-1-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 23169890HCID 23169890, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, a solution of 1-(4-methoxyphenyl)cyclopropane carboxylic acid (2.00 g, 10.4 mmol) in tetrahydrofuran (20 mL) was added with lithium aluminum hydride (513 mg, 13.5 mmol) at 0° C., and the resultant was stirred at room temperature for 2 hours. The resultant was added sequentially with water and hydrochloric acid at 0° C., stirred at room temperature for 30 min and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was dissolved in dichloromethane (15 mL). The resultant was sequentially added with molecular sieves 4β (1.80 g), N-methylmorpholine (1.83 g, 15.6 mmol) and tetrapropylammonium perruthenate (1.83 mg, 0.520 mmol) at 0° C., and stirred at room temperature for 1.5 hours. The reaction solution was filtered using celite, and concentrated in vacuo. The obtained residue was purified using column chromatography (hexane:ethyl acetate=4:1), and 1-(4-methoxyphenyl)cyclopropane carboaldehyde (1.54 g, 84.0%) was obtained.

Workup

  1. stirringstirred at room temperature for 30 min
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe obtained residue was dissolved in dichloromethane (15 mL)
  6. stirringstirred at room temperature for 1.5 hours
  7. filtrationThe reaction solution was filtered
  8. concentrationconcentrated in vacuo
  9. customThe obtained residue was purified

Sources & evidence

ORD record
ord-4a07631c94d94d14a87270c501eedc31
Source dataset
uspto-grants-2012_08
Patent number
US08236789B2

Reaction notes

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