1,1'-Carbonyldiimidazole → HCID 86725679, compound

HRID 514576Notes

Reaction equation

HRID 514576 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[Mg+2].[Cl-].[Cl-].[K+].[CH3:30][O:31][C:32](=[O:37])[CH2:33]C([O-])=O>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:13])([CH3:12])[C:9](=[O:11])[CH2:33][C:32]([O:31][CH3:30])=[O:37])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 804062-(4-Chlorophenyl)-2-methylpropionic acidHCID 2724687Potassium methyl malonateHCID 5360315Magnesium Chloride

Product 1

HCID 86725679HCID 86725679, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-chlorophenyl)-2-methylpropanoic acid (200 mg, 1.01 mmol) in THF (20 mL) was added CDI (172 mg, 1.06 mmol) at rt. The reaction mixture was stirred at rt for 2 h. Added MgCl2 (105 mg, 1.11 mmol) and 3-methoxy-3-oxopropanoic acid potassium salt (173 mg, 1.11 mmol) at rt. The mixture was stirred at 60° C. overnight. Dilute with ethyl acetate (100 mL), washed with 0.5 N HCl (20 mL×2) and brine (50 mL), dried over Na2SO4, filtered, concentrated, purified by flash column chromatography to give the title compound (60 mg, 23%) as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 1.51 (6H, s), 3.28 (2H, s), 3.67 (3H, s), 7.20-7.30 (2H, m), 7.34-7.37 (2H, m).

Workup

  1. customat rt
  2. stirringThe mixture was stirred at 60° C. overnight
  3. washwashed with 0.5 N HCl (20 mL×2) and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-f48a849a9bae491ebdf8a469bec64e25
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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