Iodoethane → 4-Hydroxy-2,2-dimethylbutyric acid ethyl ester

HRID 409479

Reaction equation

HRID 409479 reaction equation
[OH:1][CH2:2][CH2:3][C:4]([CH3:9])([CH3:8])[C:5]([O-:7])=[O:6].[K+].[CH2:11](I)[CH3:12]>CN(C=O)C>[CH2:11]([O:6][C:5](=[O:7])[C:4]([CH3:9])([CH3:8])[CH2:3][CH2:2][OH:1])[CH3:12]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 23712640Potassium 4-hydroxy-2,2-dimethylbutyrate

Product 1

HCID 596143744-Hydroxy-2,2-dimethylbutyric acid ethyl esterYield 169%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of potassium 4-hydroxy-2,2-dimethylbutyrate (1.92 mmol; 327 mg) in DMF (6 mL) is added ethyl iodide (2.30 mmol; 359 mg). The reaction mixture is stirred for 2 hours, and quenched with saturated ammonium chloride solution. The product is extracted three times with EtOAc. The combined organic layer is washed with aqueous 0.1 M HCl then brine, dried over Na2SO4, filtered, concentrated under reduced pressure to give 4-Hydroxy-2,2-dimethylbutyric acid ethyl ester (520 mg) contaminated with DMF.

Workup

  1. customquenched with saturated ammonium chloride solution
  2. extractionThe product is extracted three times with EtOAc
  3. washThe combined organic layer is washed with aqueous 0.1 M HCl
  4. dry with materialbrine, dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-de5cbd37edc14a33bced3ed4b90033ff
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Linked notes

Loading…