Ethyl Acetoacetate → ethyl 6-amino-5-cyano-4-(2-furyl)-2-methyl-4H-pyran-3-carboxylate

HRID 1020280Notes

Reaction equation

HRID 1020280 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[C:7]([C:10]#[N:11])[C:8]#[N:9].[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15]>C(O)C.N1CCCC1>[NH2:9][C:8]1[O:15][C:14]([CH3:16])=[C:13]([C:12]([O:18][CH2:19][CH3:20])=[O:17])[CH:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[C:7]=1[C:10]#[N:11]

Participants

5

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 18606Malononitrile, furfurylidene-

Product 1

HCID 3130156ethyl 6-amino-5-cyano-4-(2-furyl)-2-methyl-4H-pyran-3-carboxylateYield 55%

Reagents, catalysts & solvents 2

HCID 31268PyrrolidineCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2-furanylmethylene)malononitrile (0.72 g, 5.0 mmole) in hot ethanol (5.0 ml) was added ethyl acetoacetate (0.647 ml, 5.0 mmole) followed by 1 drop of pyrrolidine. The mixture was refluxed for 15 h. Upon cooling the mixture to room temperature a precipitate formed. The mixture was filtered to provide the desired product (0.753 g, 55%) as pinkish powder. Rf=0.4 in 50% ethyl actetate:hexanes. 1H NMR (400 MHz; CDCl3) d 7.295 (m, 1H); 6.27 (dd, 1H, J=3.1, 1.95 Hz); 6.10 (d, 1H, J=3.1 Hz); 4.63 (s, 1H); 4.50 (bs, 2H); 4.22-4.07 (m, 2H); 2.36 (s, 3H); 1.20 (t, 3H, J=7.0 Hz). LC MS shows MH+ at 275.

Workup

  1. temperatureThe mixture was refluxed for 15 h
  2. customformed
  3. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-731e20e642104bdfac565b04d03a8122
Source dataset
uspto-grants-2014_05
Patent number
US08716319B2

Reaction notes

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