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

HRID 1099025Notes

Reaction equation

HRID 1099025 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-e8087fed4e784e14aa2189c0d63d750a
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

Loading…