Ethyl cyanoacetate → HCID 13432076, compound

HRID 412835Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11]>>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:12]([C:10]#[N:11])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

Reactant 2

HCID 7764Ethyl cyanoacetate

HCID 130112-Chloroanisole

Product 1

HCID 13432076HCID 13432076, compoundYield 87%

Procedure

Method B of the above general procedure was followed using 2-chloroanisole (143 mg, 1.01 mmol) and ethyl cyanoacetate (125 mg, 1.11 mmol). The reaction mixture was purified by column chromatography on silica gel (1:3 dichloromethane/hexanes) to give the desired product (191.4 mg, 87%) as a colorless oil: 1H NMR (CDCl3) δ 7.40-7.35 (m, 2H), 7.03-6.99 (m, 1H), 6.93 (d, 8.0 Hz, 1H), 5.03 (s, 1H), 4.30-4.22 (m, 2H), 3.86 (s, 3H), 1.29 (t, 7.2 Hz, 3H). 13C{1H} NMR (CDCl3) δ 165.19, 156.48, 130.73, 129.44, 121.11, 119.11, 115.92, 111.12, 62.97, 55.72, 38.18, 13.97.

Workup

customThe reaction mixture was purified by column chromatography on silica gel (1:3 dichloromethane/hexanes)

Sources & evidence

ORD record: ord-a190d22620804943922560e712b72e44
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562989B2

Reaction notes

Loading…