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Potassium Carbonate → 2-(3-((4-Bromo-1H-pyrazol-1-yl)methyl)phenoxy)ethyl acetate

HRID 2175288
ノート
印刷プレビュー

反応式

HRID 2175288 の反応式
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]2[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=2)[CH:6]=1.[C:15]([O:18][CH2:19][CH2:20]Br)(=[O:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:15]([O:18][CH2:19][CH2:20][O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH2:7][N:5]2[CH:6]=[C:2]([Br:1])[CH:3]=[N:4]2)[CH:9]=1)(=[O:17])[CH3:16]
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

5

反応物 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 709829143-((4-Bromo-1H-pyrazol-1-yl)methyl)phenol

生成物 1

HCID 709828132-(3-((4-Bromo-1H-pyrazol-1-yl)methyl)phenoxy)ethyl acetate収率 34%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
200 °C

実験手順

A mixture of 3-((4-bromo-1H-pyrazol-1-yl)methyl)phenol (0.6 g, 2.37 mmol), 2-bromoethyl acetate (0.792 g, 4.74 mmol) and potassium carbonate (0.655 g, 4.74 mmol) in DMF (5 mL) was heated at 200° C. in a microwave reactor for 1 h. After this time, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated. The resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes) to afford the title compound (0.27 g, 34% yield) as a colorless oil. LCMS, [M+H]+=339.0. 1H NMR (400 MHz, CDCl3) δ 7.46 (s, 1H), 7.34 (s, 1H), 7.24 (dd, J=8.3, 7.6 Hz, 2H), 6.83 (dd, J=8.3, 2.4 Hz, 1H), 6.80 (d, J=7.6 Hz, 1H), 6.74 (d, J=2.4 Hz, 1H), 5.20 (s, 2H), 4.41-4.32 (m, 2H), 4.14-4.08 (m, 2H), 2.06 (s, 3H).

後処理

  1. customAfter this time, the reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe resulting residue was purified by flash chromatography (0-100% ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-ca5dc099bc244b0b8a59fb1957e7d919
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09062028B2

反応ノート

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