Ethyl 3-cyclopropyl-3-methylbutanoate → 3-Cyclopropyl-3-methylbutan-1-ol

HRID 1806893Notes

Reaction equation

HRID 1806893 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([CH:9]1[CH2:11][CH2:10]1)([CH3:8])[CH3:7])C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH:9]1([C:6]([CH3:8])([CH3:7])[CH2:5][CH2:4][OH:3])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 267154Ethyl 3-cyclopropyl-3-methylbutanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 672967843-Cyclopropyl-3-methylbutan-1-olYield 46.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Step C To a solution of 3-cyclopropyl-3-methyl-butyric acid ethyl ester (2 g, 11.75 mmol) in anhydrous tetrahydrofuran (40 mL) at 0° C. was added a tetrhydrofuran solution (1 M) of LiAlH4 (23.5 mL, 23.5 mmol) under nitrogen. The reaction mixture was stirred at 0° C. for 1 h, then poured into a ice-water. The mixture was extracted with ethyl acetate. The organic layer were separated, washed with water, aqueous HCl solution, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:10, 1:5) to give 3-cyclopropyl-3-methyl-butan-1-ol as a colorless oil (0.7 g, 46%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customThe organic layer were separated
  3. washwashed with water, aqueous HCl solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (EtOAc:hexanes=1:10, 1:5)

Sources & evidence

ORD record
ord-182355049238498ca959f91f2eec0a7d
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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