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

HRID 971005
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HRID 971005 반응식
[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]
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. customThe crude material was purified via flash column chromatography

출처 및 근거

ORD 기록
ord-3a96ff42278247ba938e4de9b3e868b5
출처 데이터셋
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07312241B2

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