Acetic Acid → HCID 67176177, compound

HRID 2362204Notes

Reaction equation

HRID 2362204 reaction equation
[CH:1]([C:3]1[N:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[CH3:16])[CH:5]=[CH:6][CH:7]=1)=O.[C:17]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:18]C([O-])=O.[K+].CC(O)=O.N1CCCCC1>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([N:4]2[CH:5]=[CH:6][CH:7]=[C:3]2[CH:1]=[CH:18][C:17]([O:23][CH2:24][CH3:25])=[O:22])=[C:9]([CH3:16])[CH:10]=1)#[N:13]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 3446434Potassium ethyl malonateHCID 58305608HCID 58305608, compound

Product 1

HCID 67176177HCID 67176177, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(2-formyl-1H-pyrrol-1-yl)-3-methylbenzonitrile (24.5 g, 116.7 mmol), DMAP (2.9 g, 23.3 mmol) and potassium monoethyl malonate (99.2 g, 583.3 mmol) in DMF (600 mL) was added AcOH (35.0 g, 583.3 mmol) and piperidine (29.8 g, 350 mmol). The resultant mixture was heated to 80° C. and stirred for 48 h. The reaction mixture was poured into cooled water and extracted with ethyl acetate (800 mL×3). The combined organic layers were washed with sat. NaHCO3 and brine, dried over Na2SO4, concentrated and purified by silica gel column chromatography (PE:EA=5:1) to afford ethyl 3-(1-(4-cyano-2-methylphenyl)-1H-pyrrol-2-yl)acrylate as a yellow oil (21.8 g, 67%).

Workup

  1. additionThe reaction mixture was poured
  2. extractionextracted with ethyl acetate (800 mL×3)
  3. washThe combined organic layers were washed with sat. NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography (PE:EA=5:1)

Sources & evidence

ORD record
ord-5bfdee9bd88447a284022db5bc4a2d8f
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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