Triethyl orthoacetate → ethyl 2-cyano-3-ethoxycrotonate

HRID 1914859Notes

Reaction equation

HRID 1914859 reaction equation
[CH3:1][C:2]([O:9][CH2:10][CH3:11])([O:6]CC)OCC.C1N=CN(C([N:19]2[CH:23]=NC=C2)=O)C=1>CC(OC(C)=O)=O>[CH2:10]([O:9][C:2](=[O:6])/[C:1](/[C:23]#[N:19])=[C:2](\[O:9][CH2:10][CH3:11])/[CH3:1])[CH3:11]

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 3033300ethyl 2-cyano-3-ethoxycrotonate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
140 °C

Procedure

To a 2000 mL round-bottom flask was added CH3C(OEt)3 (583.2 g, 3.6 mol, 1.00 eq.) and Compound [CDI] (407.2 g, 3.6 mol, 1.00 eq.) in Ac2O (1000 mL). The mixture was heated to reflux at 130-150° C. for 3 hours. The reaction mixture was concentrated to a small volume and then allowed to cool to room temperature. The mixture was allowed to sit in refrigerate overnight. The precipitated solid was filtered and dried in vacuo to give Compound [CDII] as yellow solid: LCMS (m/e) 184 (M+H).

Workup

  1. temperatureThe mixture was heated
  2. concentrationThe reaction mixture was concentrated to a small volume
  3. temperatureto cool to room temperature
  4. filtrationThe precipitated solid was filtered
  5. customdried in vacuo
  6. customto give Compound [CDII] as yellow solid

Sources & evidence

ORD record
ord-696b4a66b3194132a99acea4336daa5a
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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