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

HRID 1662351노트

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HRID 1662351 반응식
[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

참가 물질

4

반응물 2

HCID 24386Thionyl Chloride2회HCID 57705661(2-(1,1-Dimethylethyl)-3'-(ethyloxy)-1,1'-biphenyl-4-yl)methanol

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-015d28a433084345ba5ed0608a10b756
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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