Water → Ethyl 3-cyclopropyl-3-methylbutanoate

HRID 1806892Notes

Reaction equation

HRID 1806892 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([C:11]([CH:14]1[CH2:16][CH2:15]1)([CH3:13])[CH3:12])C(OCC)=O)[CH3:2].[Li+].[Cl-].O>CS(C)=O>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:11]([CH:14]1[CH2:15][CH2:16]1)([CH3:12])[CH3:13])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 672971112-(1-Cyclopropyl-1-methylethyl)malonic acid diethyl ester

Product 1

HCID 267154Ethyl 3-cyclopropyl-3-methylbutanoateYield 66%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
170 °C

Procedure

Step B To a solution of 2-(1-cyclopropyl-1-methyl-ethyl)-malonic acid diethyl ester (4.3 g, 17.8 mmol) in DMSO (30 mL) was added LiCl (1.5 g, 35.6 mmol) and H2O (0.3 mL, 17.8 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-cyclopropyl-3-methyl-butyric acid ethyl ester as a colorless oil (2 g, 66%).

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-a645a84719a74149b875c672e7eb5e82
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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