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p-Toluenesulfonic acid monohydrate → 3-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenoxy)propane-1,2-diol

HRID 1172927
ノート
印刷プレビュー

反応式

HRID 1172927 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]4[CH2:29][O:28]C(C)(C)[O:26]4)=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH:25]([OH:26])[CH2:29][OH:28])=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 595565303-(3-Chloro-4-isopropoxyphenyl)-5-(4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1,2,4-oxadiazole

生成物 1

HCID 498307383-(4-(3-(3-Chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenoxy)propane-1,2-diol収率 88%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
70 °C

実験手順

3-(3-chloro-4-isopropoxyphenyl)-5-(4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1,2,4-oxadiazole (0.1 g, 0.225 mmol) and p-toluenesulfonic acid monohydrate (8.55 mg, 0.045 mmol) were added in methanol (2.4 mL). The reaction mixture was heated at 70° C. for 16 hr. The solution was cooled, methanol (1.5 mL) was added to the mixture and recrystallized, the resulted suspension was filtered, the solid was washed by abundant water to afford 3-(4-(3-(3-chloro-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)phenoxy)propane-1,2-diol (0.08 g, 0.198 mmol, 88% yield) as white solid. LC/MS (Purity QC) Rt=2.97 min.; MS m/z: 405.18 (M+H)+. 1H NMR (400 MHz, Solvent d-DMSO) ppm 8.16-8.09 (m, 2H), 8.05 (d, J=2.13 Hz, 1H), 7.99 (dd, J=8.64, 2.15 Hz, 1H), 7.38 (d, J=9.05 Hz, 1H), 7.25-7.16 (m, 2H), 5.03 (d, J=5.19 Hz, 1H), 4.87-4.78 (m, 1H), 4.72 (t, J=5.68 Hz, 1H), 4.15 (dd, J=3.97, 10.01 Hz, 1H), 4.01 (dd, J=6.20, 10.03 Hz, 1H), 3.84 (dt, J=4.04, 5.69, 5.91 Hz, 1H), 3.47 (t, J=5.84 Hz, 2H), 1.35 (d, J=6.03 Hz, 6H).

後処理

  1. temperatureThe solution was cooled
  2. customrecrystallized
  3. filtrationthe resulted suspension was filtered
  4. washthe solid was washed by abundant water

出典と根拠

ORDレコード
ord-84140e2db22a45a591698e4855c743dc
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07834039B2

反応ノート

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