Water → 3-Ethyl-3-methyl-pentanoic acid methyl ester

HRID 1806946Notes

Reaction equation

HRID 1806946 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([C:9]([CH2:13][CH3:14])([CH3:12])[CH2:10][CH3:11])C(OC)=O.[Li+].[Cl-].O>CS(C)=O>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:9]([CH2:13][CH3:14])([CH3:12])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 866403902-(1-Ethyl-1-methyl-propyl)-malonic acid dimethyl ester

Product 1

HCID 134430493-Ethyl-3-methyl-pentanoic acid methyl esterYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
170 °C

Procedure

Step B To a solution of 2-(1-ethyl-1-methyl-propyl)-malonic acid dimethyl ester (3 g, 14 mmol) in DMSO (30 mL) was added LiCl (1.2 g, 28 mmol) and H2O (0.25 mL, 14 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 to give 3-ethyl-3-methyl-pentanoic acid methyl ester as a yellow oil (1.5 g, 68%).

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

Sources & evidence

ORD record
ord-d17603577ee94ee299d4a285500fba99
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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