Lithium Chloride → HCID 57457660, compound

HRID 551088Notes

Reaction equation

HRID 551088 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH:11](C(OC)=O)[C:12]([O:14][CH3:15])=[O:13])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1.[Cl-].[Li+]>CS(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([N+:20]([O-:22])=[O:21])[C:5]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 2

HCID 433294Lithium ChlorideHCID 57457659HCID 57457659, compound

Product 1

HCID 57457660HCID 57457660, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of dimethyl 2-(4-fluoro-2,6-dinitrophenyl)malonate from Step A (20.5 g, 64.9 mmol) and lithium chloride (5.50 g, 130 mmol) in DMSO (120 mL) and water (2.34 mL) was heated at 90° C. for 3 h, then cooled and poured onto H2O (400 mL). The aqueous layer was extracted with Et2O (3×250 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexanes:EtOAc—100:0 to 80:20, to give the title compound. MS: m/z=259 (M+1).

Workup

  1. temperaturecooled
  2. additionpoured onto H2O (400 mL)
  3. extractionThe aqueous layer was extracted with Et2O (3×250 mL)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of hexanes

Sources & evidence

ORD record
ord-720bb077cbb04294b61489e4a9f9dd58
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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