4-Cyanobenzaldehyde → 4-(2-Cyano-3-oxopent-1-enyl)benzonitrile

HRID 403499Notes

Reaction equation

HRID 403499 reaction equation
[O:1]=[C:2]([CH2:6][CH3:7])[CH2:3][C:4]#[N:5].[CH:8]([C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)=O.N1CCC[C@H]1C(O)=O>CCO>[C:4]([C:3]([C:2](=[O:1])[CH2:6][CH3:7])=[CH:8][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)#[N:5]

Participants

5

Reactant 3

HCID 660424-CyanobenzaldehydeHCID 145742L-ProlineHCID 99203693-oxopentanenitrile

Product 1

HCID 683795824-(2-Cyano-3-oxopent-1-enyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
22 °C

Procedure

To a 1000 ml, four-necked flask equipped with an overhead stirrer, a thermocouple and a condenser was charged with 3-oxopentanenitrile (23) (21.8 g, 135 mmol, 60%) of, 4-formylbenzonitrile (17.7 g, 135 mmol), L-proline (3.65 g, 27 mmol, 0.2 eq) and 200 ml of EtOH. The mixture was stirred at 22° C. for 16 hours and concentrated to a volume of approximately 120 ml. 100 ml of MTBE was added and the mixture was stirred at 22° C. for about 30 min. The precipitate was collected by vacuum filtration. The solid was washed with 50 ml of MTBE. It was dried in a vacuum oven at 50° C. to give the product 24 as a off white solid. 1H NMR (500 MHz, CDCl3) δ (ppm): 8.20 (s, 1H), 8.10 (d, 2H), 7.81 (d, 2H), 3.00 (m, 2H), 1.28 (t, 3H).

Workup

  1. customTo a 1000 ml, four-necked flask equipped with an overhead stirrer
  2. concentrationconcentrated to a volume of approximately 120 ml
  3. addition100 ml of MTBE was added
  4. stirringthe mixture was stirred at 22° C. for about 30 min
  5. filtrationThe precipitate was collected by vacuum filtration
  6. washThe solid was washed with 50 ml of MTBE
  7. customIt was dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-2ff135110a92410aaea068f09fe414cd
Source dataset
uspto-grants-2014_06
Patent number
US08748435B2

Reaction notes

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