Water → Methyl 3,3-diethylpentanoate

HRID 1806938Notes

Reaction equation

HRID 1806938 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]([C:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[CH2:10][CH3:11])C(OC)=O.[Li+].[Cl-].O>CS(C)=O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 866403882-(1,1-Diethyl-propyl)-malonic acid dimethyl ester

Product 1

HCID 12714308Methyl 3,3-diethylpentanoateYield 100.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
170 °C

Procedure

Step C To a solution of 2-(1,1-diethyl-propyl)-malonic acid dimethyl ester (2.5 g, 11 mmol) in DMSO (30 mL) was added LiCl (0.91 g, 21.6 mmol) and H2O (0.19 mL, 11 mmol). The reaction mixture was heated at 170° C. for 4 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 3,3-diethyl-pentanoic acid methyl ester as a yellow oil (1.9 g, 100%).

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-f19b024884594e3b844d6e624dc81725
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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