Dimethylformamide → Methyl 1-(4-methoxyphenyl)-cyclopropanecarboxylate

HRID 2245921Notes

Reaction equation

HRID 2245921 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[C:15](Cl)(=O)C(Cl)=O.CN(C)C=O>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2([C:12]([O:14][CH3:15])=[O:13])[CH2:10][CH2:11]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 855751-(4-Methoxyphenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 13707544Methyl 1-(4-methoxyphenyl)-cyclopropanecarboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Methoxyphenyl)cyclopropanecarboxylic acid (0.970 g, 5.05 mmol) in dichloromethane (DCM; 5 mL) was mixed with oxalyl chloride (1.28 mL, 15.1 mmol) followed by addition of a drop of N,N-dimethylformamide (DMF; 20 μL). The mixture was stirred at room temperature (RT) for 2 h. The solvent was evaporated. The residue was co-evaporated with toluene (2×), and dissolved in DCM (10 mL). The solution was cooled at −10° C., and then methanol (3 mL) was carefully added to the solution. The resulting mixture was allowed to warm to RT. The volatiles were evaporated under reduced pressure to afford the desired product (1.03 g, 99%).

Workup

  1. customThe solvent was evaporated
  2. dissolutiondissolved in DCM (10 mL)
  3. temperatureThe solution was cooled at −10° C.
  4. additionmethanol (3 mL) was carefully added to the solution
  5. temperatureto warm to RT
  6. customThe volatiles were evaporated under reduced pressure

Sources & evidence

ORD record
ord-c0005e9b31e344cba9d0409206e442c1
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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