Methyl iodide → Methyl 1-(p-tolyl)cyclopropanecarboxylate

HRID 2170618

Reaction equation

HRID 2170618 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[CH2:14]1CCN2C(=NCCC2)CC1.CI>C(#N)C.CCOC(C)=O>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([C:7]2([C:10]([O:12][CH3:14])=[O:11])[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 986391-(p-Tolyl)cyclopropanecarboxylic acid

Product 1

HCID 57443305Methyl 1-(p-tolyl)cyclopropanecarboxylateYield 64%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(p-tolyl)cyclopropanecarboxylic acid (900 mg, 5.1 mmol) in acetonitrile (20 mL) was added DBU (917 μL) followed by methyl iodide (1.91 mL). The resulting solution was heated at reflux overnight, and then diluted with AcOEt. The mixture was washed with a 0.5 N HCl solution, a saturated solution of NaHCO3, and brine, dried on MgSO4, and concentrated. The resulting colorless oil was purified by chromatography on silica gel (Hexane/ethyl acetate 9/1) to afford the title compound as a colorless oil (622 mg, 64%).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux overnight
  3. washThe mixture was washed with a 0.5 N HCl solution
  4. dry with materiala saturated solution of NaHCO3, and brine, dried on MgSO4
  5. concentrationconcentrated
  6. customThe resulting colorless oil was purified by chromatography on silica gel (Hexane/ethyl acetate 9/1)

Sources & evidence

ORD record
ord-26cd73b39ef24724b7e91aee27671a72
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Linked notes

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