Dimethylformamide → Cyclobutanecarboxylic acid, 3-methylene-, propyl ester

HRID 519637Notes

Reaction equation

HRID 519637 reaction equation
[CH2:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1.[H-].[Na+].CN(C)C=O.[CH2:16](I)[CH2:17][CH3:18]>C(OCC)(=O)C>[CH2:1]=[C:2]1[CH2:5][CH:4]([C:6]([O:8][CH2:16][CH2:17][CH3:18])=[O:7])[CH2:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 274753-Methylenecyclobutanecarboxylic acidHCID 336431-Iodopropane

Product 1

HCID 45090160Cyclobutanecarboxylic acid, 3-methylene-, propyl esterYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-methylidenecyclobutanecarboxylic acid (18 g), sodium hydride (6.9 g) and N,N-dimethylformamide (300 mL) was stirred at room temperature for 10 min, propyl iodide (17 mL) was added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was diluted with ethyl acetate, washed with 5% aqueous potassium hydrogensulfate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by distillation (45-50° C., 2 mmHg) to give the title compound as a colorless oil (16 g, 66%).

Workup

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. washwashed with 5% aqueous potassium hydrogensulfate solution
  3. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. distillationthe residue was purified by distillation (45-50° C., 2 mmHg)

Sources & evidence

ORD record
ord-915141172c734e4ca53d7f7c7f24bb7f
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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