Dimethylformamide → Methyl 1-phenylcyclopropane-1-carboxylate

HRID 504337Notes

Reaction equation

HRID 504337 reaction equation
CI.[C:3]1([C:9]2([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:15](=O)([O-])[O-].[K+].[K+].CN(C)C=O>CCOCC>[C:3]1([C:9]2([C:12]([O:14][CH3:15])=[O:13])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 802061-Phenylcyclopropanecarboxylic acid

Product 1

HCID 12861006Methyl 1-phenylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl iodide (2.8 mL, 0.045 mol) was added to a mixture of 1-phenylcyclopropane carboxylic acid (4.9 g, 0.030 mol) and potassium carbonate (8.3 g, 0.060 mol) in N,N-dimethylformamide (40 mL, 0.5 mol) at room temperature and then stirred for 1 hour. The mixture was diluted with ether, washed with water (×2) and brine successively, dried and concentrated to give the desired product.

Workup

  1. washwashed with water (×2) and brine successively
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-161c70734bce4fa4bad8ad16e79d102d
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

Loading…