Thionyl Chloride → 4-(Chloromethyl)-2-(1,1-dimethylethyl)-3'-(ethyloxy)-1,1'-biphenyl

HRID 1662351ノート

反応式

HRID 1662351 の反応式
[CH3:1][C:2]([C:5]1[CH:10]=[C:9]([CH2:11]O)[CH:8]=[CH:7][C:6]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH3:21])[CH:14]=1)([CH3:4])[CH3:3].S(Cl)([Cl:24])=O>C(Cl)Cl>[Cl:24][CH2:11][C:9]1[CH:8]=[CH:7][C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH3:21])[CH:14]=2)=[C:5]([C:2]([CH3:4])([CH3:3])[CH3:1])[CH:10]=1

参加物

4

反応物 2

HCID 24386Thionyl Chloride2 回HCID 57705661(2-(1,1-Dimethylethyl)-3'-(ethyloxy)-1,1'-biphenyl-4-yl)methanol

生成物 1

HCID 577055054-(Chloromethyl)-2-(1,1-dimethylethyl)-3'-(ethyloxy)-1,1'-biphenyl収率 74%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A dry, round bottom flask containing 41.2 (0.72 g, 2.53 mmol) and DCM (9.0 mL) was cooled to 0° C. After 15 minutes, thionyl chloride (1.0 mL, 13.7 mmol) was carefully added dropwise at 0° C. Upon complete addition of thionyl chloride, the mixture was allowed to warm to room temperature and stirred overnight. After 20 hours, the reaction was concentrated under reduced pressure. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-15% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to provide 41.3 as a colorless oil (0.57, 74%). 1H NMR (500 MHz, CDCl3) δ ppm 7.54 (1H, d, J=2.0 Hz), 7.25 (2H, m), 7.04 (1H, d, J=7.4 Hz), 6.90 (3H, m), 4.65 (2H, s), 4.05 (2H, m), 1.43 (3H, t, J=7.0 Hz), 1.24 (9H, s).

後処理

  1. temperatureto warm to room temperature
  2. waitAfter 20 hours
  3. concentrationthe reaction was concentrated under reduced pressure
  4. customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-15% EtOAc in hexanes)
  5. additionFractions containing the desired product
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-015d28a433084345ba5ed0608a10b756
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

反応ノート

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