Acetone → 4-Ethoxy-but-2-ynoic acid methyl ester

HRID 237863Notes

Reaction equation

HRID 237863 reaction equation
[CH2:1]([O:3][CH2:4][C:5]#CCO)[CH3:2].C[C:10]([CH3:12])=[O:11].OS(O)(=O)=O.O=[Cr](=O)=O.C[C:23](C)=[O:24]>O>[CH3:23][O:24][C:10](=[O:11])[C:12]#[C:2][CH2:1][O:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 180AcetoneHCID 127868104-Ethoxybut-2-yn-1-olHCID 131709961Jones' reagent

Product 1

HCID 645351684-Ethoxy-but-2-ynoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 4-ethoxy-but-2-yn-1-ol (1 g, 8.76 mmol) in acetone (26 mL) at 0° C. was added dropwise Jones reagent. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with water and extracted with methyl acetate. The organic layers were combined, dried (Na2SO4), and concentrated. The resulting 4-ethoxy-but-2-ynoic acid was methylated (TMSCHN2 (2 M), MeOH/toluene, room temperature, 3 hours) to afford 0.66 g of the title compound as a clear oil.

Workup

  1. extractionextracted with methyl acetate
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custom(TMSCHN2 (2 M), MeOH/toluene, room temperature, 3 hours)

Sources & evidence

ORD record
ord-affedccda82848c7b8659857e413d542
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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