Water → HCID 58288282, compound

HRID 1476136Notes

Reaction equation

HRID 1476136 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:11](C(OCC)=O)[C:12]([O:14][CH2:15][CH3:16])=[O:13])([CH3:10])[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])([CH3:10])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 3283Diethyl EtherHCID 433294Lithium ChlorideHCID 58288432HCID 58288432, compound

Product 1

HCID 58288282HCID 58288282, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 796 mg (2.55 mmol) of diethyl [2-(4-chlorophenyl)propan-2-yl]malonate, 216 mg (5.10 mmol) of lithium chloride and 46 μl (2.55 mmol) of water in 5 ml of DMSO was heated to reflux and stirred at this temperature for 4 h. After cooling to room temperature, 20 ml of diethyl ether and 20 ml of water were added to the reaction mixture. After separation of the phases, the organic phase was washed three more times with water, and the organic phase was dried over magnesium sulphate and then concentrated to dryness. The crude product was purified by preparative HPLC (mobile phase methanol/water 70:30). This gave 276 mg of the title compound (45% of theory).

Workup

  1. temperatureto reflux
  2. customAfter separation of the phases
  3. washthe organic phase was washed three more times with water
  4. dry with materialthe organic phase was dried over magnesium sulphate
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by preparative HPLC (mobile phase methanol/water 70:30)

Sources & evidence

ORD record
ord-7c0882a1fdd44c1e96594d40bae7f3a9
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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