Dichloromethane → HCID 86730673、化合物

HRID 332887ノート

反応式

HRID 332887 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:13]=[CH:14][C:15](C=O)=[N:16][CH:17]=3)=[C:9]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[S:8][C:7]=2[CH:28]=1.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:36][C:37]([O:39][CH3:40])=[O:38])C=CC=CC=1.[CH2:53](Cl)Cl>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:13]=[CH:14][C:15](/[CH:53]=[CH:36]/[C:37]([O:39][CH3:40])=[O:38])=[N:16][CH:17]=3)=[C:9]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[S:8][C:7]=2[CH:28]=1

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 867306725-((6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)picolinaldehyde

生成物 1

HCID 86730673HCID 86730673、化合物収率 32%

実験手順

To a solution of 5-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)picolinaldehyde (0.265 g, 0.68 mmol) in DCM (3.38 mL) at 0° C. was added methyl 2-(triphenylphosphoranylidene)acetate (0.543 g, 1.63 mmol) and the reaction was stirred at room temperature for 18 h. Upon completion the mixture was concentrated in vacuo to afford crude material which was purified by column chromatography (SiO2, 0-25% EtOAc/heptanes) to afford (E)-methyl 3-(5-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)pyridin-2-yl)acrylate (96 mg, 0.22 mmol, 32% yield). 1H NMR (400 MHz, CDCl3) δ ppm=3.70-3.75 (m, 6H), 3.79-3.83 (m, 3H), 6.70 (d, J=15.66 Hz, 1H), 6.77-6.88 (m, 3H), 7.02 (dd, J=8.59, 3.03 Hz, 1H), 7.17 (s, 1H), 7.18-7.22 (m, 2H), 7.48-7.59 (m, 3H), 8.42 (d, J=2.53 Hz, 1H). LC/MS (m/z, MH+): 448.3.

後処理

  1. concentrationUpon completion the mixture was concentrated in vacuo
  2. customto afford crude material which
  3. customwas purified by column chromatography (SiO2, 0-25% EtOAc/heptanes)

出典と根拠

ORDレコード
ord-22d6f7ede3db4d6280dfca7ad3a71904
出典データセット
uspto-grants-2014_11
特許番号
US08877801B2

反応ノート

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