Ethyl cyanoacetate → Ethyl 2-(3,4-Methylenedioxyphenyl)cyanoacetate

HRID 412834Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:9][O:10][C:4]=2[CH:3]=1.[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12]>>[CH2:9]1[O:8][C:5]2[CH:6]=[CH:7][C:2]([CH:13]([C:11]#[N:12])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:3][C:4]=2[O:10]1

Participants

Reactant 2

HCID 7764Ethyl cyanoacetate

HCID 1389665-Chloro-1,3-benzodioxole

Product 1

HCID 10900525Ethyl 2-(3,4-Methylenedioxyphenyl)cyanoacetateYield 82%

Procedure

Method B of the above general procedure was followed using 4-chloro-1,2-(methylenedioxy)benzene (157 mg, 1.00 mmol) and ethyl cyanoacetate (124 mg, 1.10 mmol). The reaction mixture was purified by column chromatography on silica gel (1:3 dichloromethane/hexanes) to give the desired product (191 mg, 82%) as a colorless oil: 1H NMR (CDCl3) δ 6.93-6.90 (m, 2H), 6.83-6.80 (m, 1H), 6.00 (s, 2H), 4.62 (s, 1H), 4.30-4.19 (m, 2H), 1.29 (t, 7.2 Hz, 3H). 13C{1H} NMR (CDCl3) δ 165.07, 148.46, 148.44, 123.33, 121.76, 115.75, 108.79, 108.25, 101.68, 63.34, 43.31, 13.92. Anal. Calcd. for C12H11NO4: C, 61.80; H, 4.75; N, 6.01. Found: C, 62.08: H, 4.62: N, 6.13.

Workup

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

Sources & evidence

ORD record: ord-65e1e4589a7b4bac87d107f814b0272f
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562989B2

Reaction notes

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