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

HRID 626208노트

반응식

HRID 626208 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
85 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-b4e4481d0c3f4f2cb2003307e79e76f4
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309211B2

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