Water → HCID 67469173, compound

HRID 1019757Notes

Reaction equation

HRID 1019757 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH:13](C(OC)=O)[C:14](OC)=[O:15].[Cl-].[Na+].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH2:13][CH2:14][OH:15]

Participants

5

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 25156888HCID 25156888, compound

Product 1

HCID 67469173HCID 67469173, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of dimethyl 2-(2-chloro-5-methoxy-4-nitrophenyl)malonate (15.5 g, 48.7 mmol), sodium chloride (5.70 g, 97.5 mmol) and water (0.876 mL, 48.7 mmol) in DMSO (200 mL) was heated to 120° C. for 2 hours. The cooled reaction mixture was partitioned between water (1000 mL) and EtOAc (200 mL) and the separated aqueous phase was extracted with EtOAc (200 mL). The combined organic extracts were washed with brine (150 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on neutral silica gel using 3-10% EtOAc in hexane to give the title compound (10.2 g, 86%) as a solid.

Workup

  1. customThe cooled reaction mixture
  2. customwas partitioned between water (1000 mL) and EtOAc (200 mL)
  3. extractionthe separated aqueous phase was extracted with EtOAc (200 mL)
  4. washThe combined organic extracts were washed with brine (150 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on neutral silica gel using 3-10% EtOAc in hexane

Sources & evidence

ORD record
ord-6d5a1271b31e406b915f79c5544bf587
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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