Malononitrile → HCID 86678961, compound

HRID 2203314Notes

Reaction equation

HRID 2203314 reaction equation
C1CCN2C(=NCCC2)CC1.[C:12](#[N:16])[CH2:13][C:14]#[N:15].Br[C:18]([C:25]1[N:29]=[C:28]([CH3:30])[O:27][N:26]=1)([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C1COCC1>[C:14]([CH:13]([C:12]#[N:16])[C:18]([CH3:24])([C:25]1[N:29]=[C:28]([CH3:30])[O:27][N:26]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])#[N:15]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86678960HCID 86678960, compound

Product 1

HCID 86678961HCID 86678961, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

DBU (2.56 mL, 8.1 mmol) was added dropwise to a −78° C. THF (20 mL) solution of malononitrile (1.12 g, 17 mmol) and the intermediate from Step C (1.49 g, 5.66 mmol). The reaction solution was stirred at −78° C. for 15 minutes and then at room temperature for 1 hour. The solution was then concentrated and the residue purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR δ (ppm) (CHCl3-d): 4.79 (1H, s), 4.30 (2H, dd, J=7.1, 2.6 Hz), 2.64 (3H, s), 2.02 (3H, s), 1.31-1.25 (3H, m).

Workup

  1. waitat room temperature for 1 hour
  2. concentrationThe solution was then concentrated
  3. customthe residue purified by silica gel chromatography
  4. customto give the indicated product

Sources & evidence

ORD record
ord-65e72e6c620e4ffeb8498d3280cd2fbe
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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