Piperidine → (E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate

HRID 333326

Reaction equation

[C:1]([CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2].[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH:15]=O.N1CCCCC1>CCO>[C:1](/[C:3](=[CH:15]\[C:14]1[CH:17]=[CH:18][C:19]([Cl:20])=[C:12]([Cl:11])[CH:13]=1)/[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of tert-butyl cyanoacetate (2.52 ml, 17.63 mmol), 3,4-dichlorobenzaldehyde (2.57 g, 14.69 mmol) and piperidine (0.145 ml, 1.469 mmol) in EtOH (50 ml) was allowed to stir at 80° C. for 15 hours, and then cooled to ambient temperature. A half volume of the solvent was evaporated, and 400 ml of water was added to the resulting mixture. The precipitated solid was collected and washed with 5% iPrOH/H2O (200 ml). The solid was dried under reduced pressure to give (E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate (3.577 g); Retention time=1.61 minutes (condition A); MS (ES+)=315.1 (m+18).

Workup

temperaturecooled to ambient temperature
customA half volume of the solvent was evaporated
addition400 ml of water was added to the resulting mixture
customThe precipitated solid was collected
washwashed with 5% iPrOH/H2O (200 ml)
customThe solid was dried under reduced pressure

Sources & evidence

ORD record: ord-1491605790b04672bdfb6bed058d5069
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877815B2

Linked notes

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