Malononitrile → Dihydro-2H-pyran-4,4(3H)-dicarbonitrile
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]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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, 4 H) 3.77-3.96 (m, 4 H).
Workup
- temperaturecooled to ambient temperature
- concentrationThe mixture was concentrated in vacuo
- additionthe resulting residue was diluted with ethyl acetate
- washwashed three times with water
- customdried overnight under high vacuum
Sources & evidence
- ORD record
- ord-d7d02786dd2448a9b0fc6b7ed767ede7
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415381B2
Reaction notes
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