Methyl iodide → Methyl 4-cyclobutyl-5-formyl-2-methylbenzoate

HRID 1487953Notes

Reaction equation

HRID 1487953 reaction equation
[CH:1]1([C:5]2[C:13]([CH:14]=[O:15])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH3:16])[CH:6]=2)[CH2:4][CH2:3][CH2:2]1.[C:17](=O)(O)[O-].[Na+].CI>CN(C)C=O.CCOC(C)=O>[CH:1]1([C:5]2[C:13]([CH:14]=[O:15])=[CH:12][C:8]([C:9]([O:11][CH3:17])=[O:10])=[C:7]([CH3:16])[CH:6]=2)[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 866725464-Cyclobutyl-5-formyl-2-methylbenzoic acid2×

Product 1

HCID 90021669Methyl 4-cyclobutyl-5-formyl-2-methylbenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a mixture of 4-cyclobutyl-5-formyl-2-methylbenzoic acid (compound 82.4, 500 mg, 2.29 mmol) in N,N-dimethylformamide (10 mL) and sodium bicarbonate (390 mg, 4.64 mmol). With stirring, methyl iodide (430 μL, 6.90 mmol) was added drop-wise and the resulting mixture was stirred for 5 h at room temperature. The reaction was then diluted with EtOAc (50 mL) and the mixture was washed with brine (4×10 mL). The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure to yield 0.40 g (crude) of the title compound as a brown oil

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. stirringthe resulting mixture was stirred for 5 h at room temperature
  3. washthe mixture was washed with brine (4×10 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f05c49b313434ff998bc128638bd57ac
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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