Water → 3-Methyl-3-(5-methyl-furan-2-yl)-butyric acid methyl ester

HRID 1807021Notes

Reaction equation

HRID 1807021 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([C:9]([CH3:17])([C:11]1[O:12][C:13]([CH3:16])=[CH:14][CH:15]=1)[CH3:10])C(OC)=O.[Li+].[Cl-].O>CS(C)=O>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:9]([CH3:10])([C:11]1[O:12][C:13]([CH3:16])=[CH:14][CH:15]=1)[CH3:17]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 143572892-[1-Methyl-1-(5-methyl-furan-2-yl)-ethyl]-malonic acid dimethyl ester

Product 1

HCID 143572913-Methyl-3-(5-methyl-furan-2-yl)-butyric acid methyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
170 °C

Procedure

Step C To a solution of 2-[1-methyl-1-(5-methyl-furan-2-yl)-ethyl]-malonic acid dimethyl ester (2.5 g, 9.8 mmol) in DMSO (30 mL) was added LiCl (1 g, 23.7 mmol) and H2O (0.17 mL, 9.8 mmol). The reaction mixture was heated at 170° C. for 3 h, then poured into a ice-water, extracted with ethyl acetate. The organic layer were separated, washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:20, 1:20) to give 3-methyl-3-(5-methyl-furan-2-yl)-butyric acid methyl ester as a colorless oil (1.5 g, 78%).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer were separated
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc:hexanes=1:20, 1:20)

Sources & evidence

ORD record
ord-2b15ec153c234f4c93a696aebb54c7b3
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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