Water → HCID 70873034, compound

HRID 2402352Notes

Reaction equation

HRID 2402352 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:13](C(OC)=O)[C:14]([O:16][CH3:17])=[O:15])([CH:10]([CH3:12])[CH3:11])[CH3:9])=[CH:4][CH:3]=1.[Cl-].[Li+].O.C(OCC)C>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:9])([CH:10]([CH3:11])[CH3:12])[CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 433294Lithium ChlorideHCID 70914950HCID 70914950, compound

Product 1

HCID 70873034HCID 70873034, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.38 g (10.81 mmol) of dimethyl [2-(4-chlorophenyl)-3-methylbutan-2-yl]malonate, 0.92 g (21.61 mmol) of lithium chloride and 0.2 ml of water in 10 ml of DMSO were heated under reflux for 4 h. After cooling, about 50 ml of diethyl ether were added to the reaction solution, and the phases were separated. The organic phase was washed twice with water, dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 2.3 g (84% of theory) of the target compound.

Workup

  1. temperatureunder reflux for 4 h
  2. temperatureAfter cooling
  3. customthe phases were separated
  4. washThe organic phase was washed twice with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-7b8d35e025f743a5aed8be94412ddee0
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

Loading…