Malononitrile → Dihydro-2H-pyran-4,4(3H)-dicarbonitrile

HRID 1623250Notes

Reaction equation

HRID 1623250 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].Br[CH2:7][CH2:8][O:9][CH2:10][CH2:11]Br.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[O:9]1[CH2:10][CH2:11][C:2]([C:1]#[N:5])([C:3]#[N:4])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 21521Bis(2-bromoethyl) etherHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 14537194Dihydro-2H-pyran-4,4(3H)-dicarbonitrileYield 80.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of malononitrile (0.991 g, 15 mmol), 1-bromo-2-(2-bromoethoxy)ethane (3.83 g, 16.50 mmol) and DBU (4.97 ml, 33.0 mmol) in DMF (6 ml) was heated at about 85° C. for 3 hours, and then cooled to ambient temperature. The mixture was concentrated in vacuo, the resulting residue was diluted with ethyl acetate, washed three times with water and dried overnight under high vacuum to yield the desired product as a light brown solid (1.65 g). GC-MS: 136 [M]; Retention time=5.76 min. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.14-2.32 (m, 4H) 3.77-3.96 (m, 4H).

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. additionthe resulting residue was diluted with ethyl acetate
  4. washwashed three times with water
  5. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-380913a1ebf1496eb63629eda3cab993
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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