Diethyl (cyanomethyl)phosphonate → 3,3-Bis(3,4,5-Trimethoxyphenyl)Acrylonitrile

HRID 971005Notes

Reaction equation

HRID 971005 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(OP([CH2:35][C:36]#[N:37])(=O)OCC)C.C[Si]([N-][Si](C)(C)C)(C)C.[K+].O1C2C=CC(C(C3C=C(OC)C=C(OC)C=3)=CC#N)=CC=2OCC1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)=[CH:35][C:36]#[N:37])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 75676Diethyl (cyanomethyl)phosphonateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 15273941Bis-(3,4,5-trimethoxy-phenyl)-methanoneHCID 692032153-(2,3-Dihydrobenzo[1,4]dioxin-6-yl)-3-(3,5-dimethoxyphenyl)acrylonitrile

Product 1

HCID 103179163,3-Bis(3,4,5-Trimethoxyphenyl)AcrylonitrileYield 209.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Bis-(3,4,5-trimethoxy-phenyl)-methanone (0.32 g, 0.88 mmol), cyanomethylphosphonic acid diethyl ester (0.28 ml, 0.31 mmol) in anhydrous THF (20 ml), and potassium bis(trimethylsilyl)amide (0.35 g, 1.8 mmol) were treated in the same manner as described above for the synthesis of 3-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-3-(3,5-dimethoxyphenyl)acrylonitrile. The crude material was purified via flash column chromatography to give 3,3-Bis-(3,4,5-trimethoxy-phenyl)-acrylonitrile as a solid (0.25 g, 74%): mp, 146-148° C.; 1HNMR (DMSO-d6) δ 6.69 (d, J=5 Hz, 4H, Ar), 6.32 (s, 1H, CH), 3.77-3.72 (m, 18H, 6OCH3); 13C NMR (DMSO-d6) δ 161.27, 152.69, 152.61, 139.60, 138.66, 133.06, 131.94, 118.43, 107.09, 106.23, 100.40, 95.21, 60.13, 60.10, 56.08, 56.07; Anal. Calcd. For C21H24NO6: C, 65.44; H, 6.02; N, 3.63. Found: C, 65.08; H, 5.99; N, 3.45.

Workup

  1. customThe crude material was purified via flash column chromatography

Sources & evidence

ORD record
ord-3a96ff42278247ba938e4de9b3e868b5
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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