Ethyl cyanoacetate → 932750-29-3

HRID 1846245Notes

Reaction equation

HRID 1846245 reaction equation
[CH2:1]([O:3][C:4](OCC)(OCC)[CH3:5])[CH3:2].[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13]>C(OC(=O)C)(=O)C>[C:12](/[C:14](=[C:1](\[O:3][CH2:4][CH3:5])/[CH3:2])/[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 66221Triethyl orthoacetate

Product 1

HCID 6387109932750-29-3Yield 18.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 1,1,1-triethoxyethane (25 g, 154.11 mmol, 1.00 equiv), ethyl 2-cyanoacetate (15 g, 132.61 mmol, 0.86 equiv) in acetic anhydride (100 mL) was stirred at 95° C. for 8 h. The resulting mixture was cooled to room temperature and concentrated under vacuum. The solid was collected by filtration to give 4.4 g (16%) of (E)-ethyl 2-cyano-3-ethoxybut-2-enoate as a yellow solid. 1H-NMR (300 MHz, CDCl3): δ 4.31-4.19 (m, 4H), 2.61 (s, 3H), 1.46 (t, J=6.3 Hz, 3H), 1.32 (t, J=6.3 Hz, 3H) ppm. LCMS (method D, ESI): RT=1.31 min, m/z=184.0 [M+H]+.

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-7e89a8a883124a8da44fa989a6a9a855
Source dataset
uspto-grants-2015_02
Patent number
US08952026B2

Reaction notes

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