Methylamine → 4-(2-(2,3-Dihydrobenzofuran-5-yl)-1-(4-(2-(methylamino)ethoxy)-phenyl)but-1-enyl)phenol

HRID 626208ノート

反応式

HRID 626208 の反応式
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[C:12]([C:15]2[CH:16]=[CH:17][C:18]3[O:22][CH2:21][CH2:20][C:19]=3[CH:23]=2)[CH2:13][CH3:14])=[CH:7][CH:6]=1.[CH3:31][NH2:32]>CO>[O:22]1[C:18]2[CH:17]=[CH:16][C:15]([C:12]([CH2:13][CH3:14])=[C:11]([C:24]3[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=3)[C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:32][CH3:31])=[CH:6][CH:7]=3)=[CH:23][C:19]=2[CH2:20][CH2:21]1

参加物

4

反応物 2

HCID 6329MethylamineHCID 896574494-(1-(4-(2-Chloroethoxy)phenyl)-2-(2,3-dihydrobenzofuran-5-yl) but-1-enyl)phenol

生成物 1

HCID 726804464-(2-(2,3-Dihydrobenzofuran-5-yl)-1-(4-(2-(methylamino)ethoxy)-phenyl)but-1-enyl)phenol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
85 °C

実験手順

To a stirred solution of 4-(1-(4-(2-chloroethoxy)phenyl)-2-(2,3-dihydrobenzofuran-5-yl)but-1-enyl)phenol (500 mg, 1.0 eq) in 20 mL MeOH, 10 mL CH3NH2 (aq) was added and heated at 85° C. for 24 h. The solvent was removed in vacuo, water was added to the residue and extracted with EtOAc. The extract was dried, concentrated, and purified by column chromatography to give the desired product (Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.10 & 7.01 (d, J=8.8 Hz, 2H), 6.92 (s, 1H), 6.83 (d, J=8.4 Hz, 1H), 6.82 & 6.74 (d, J=8.8 Hz, 2H), 6.79 & 6.75 (d, J=8.8 Hz, 2H), 6.57 (d, J=8.4 Hz, 1H), 6.51 & 6.45 (d, J=8.8 Hz, 2H), 4.51 (t, J=8.4 Hz, 2H), 4.10 & 3.96 (t, J=4.8 Hz, 2H), 3.09 (t, J=8.8 Hz, 2H), 3.01 & 2.93 (t, J=4.8 Hz, 2H), 2.54 & 2.50 (s, 3H), 2.39-2.46 (m, 2H), 0.90-0.94 (m, 3H); m/z=416 [M+1]+.

後処理

  1. customThe solvent was removed in vacuo, water
  2. additionwas added to the residue
  3. extractionextracted with EtOAc
  4. customThe extract was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography

出典と根拠

ORDレコード
ord-b4e4481d0c3f4f2cb2003307e79e76f4
出典データセット
uspto-grants-2016_04
特許番号
US09309211B2

反応ノート

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