Diethyl Malonate → HCID 67099548, compound

HRID 2078300Notes

Reaction equation

HRID 2078300 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Mg+2].[Cl-].[Cl-].[Cl:15][C:16]1[CH:17]=[C:18]([C:23]([CH3:28])([CH3:27])[C:24](O)=[O:25])[CH:19]=[CH:20][C:21]=1[F:22].S(Cl)(Cl)=O>C(#N)C>[Cl:15][C:16]1[CH:17]=[C:18]([C:23]([CH3:28])([CH3:27])[C:24]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[O:25])[CH:19]=[CH:20][C:21]=1[F:22]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 24386Thionyl ChlorideHCID 5360315Magnesium ChlorideHCID 57685611HCID 57685611, compound

Product 1

HCID 67099548HCID 67099548, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diethyl malonate (5.68 mL, 37.6 mmol) was dissolved in ACN (75 mL) at 0° C. MgCl2 (3.93 g, 41.3 mmol) was added to the reaction mixture in one portion and TEA (10.5 mL, 75.1 mmol) was added dropwise. 2-(3-chloro-4-fluorophenyl)-2-methylpropanoic acid (7.73 g, 35.7 mmol) was converted to the acid chloride by reaction with thionyl chloride at 65° C. for 1 hour, and the resulting acid chloride was concentrated under reduced pressure. The acid chloride was then dissolved in ACN and added dropwise via addition funnel to the initial reaction mixture. The resulting mixture was stirred at ambient temperature for 2 hours and then quenched with water, acidified with 5N HCl, diluted with 100 mL of diethyl ether, added to a separatory funnel, partitioned with water, washed with water (2×50 mL), separated, dried over Na2SO4, and concentrated in vacuo to give the title compound (7.17 g) as a light yellow oil after flash chromatography. MS m/e=359 (M+H)+.

Workup

  1. additionwas added dropwise
  2. concentrationthe resulting acid chloride was concentrated under reduced pressure
  3. dissolutionThe acid chloride was then dissolved in ACN
  4. additionadded dropwise via addition funnel to the initial
  5. customreaction mixture
  6. customquenched with water
  7. additiondiluted with 100 mL of diethyl ether
  8. additionadded to a separatory funnel
  9. custompartitioned with water
  10. washwashed with water (2×50 mL)
  11. customseparated
  12. dry with materialdried over Na2SO4
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bd84d9bfcb24680ae687626f879d658
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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