Pyridine → Benzofuran-6-YL trifluoromethanesulfonate

HRID 869865노트

반응식

HRID 869865 반응식
[O:1]1[C:5]2[CH:6]=[C:7]([OH:10])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.N1C=CC=CC=1.[O:17](S(C(F)(F)F)(=O)=O)[S:18]([C:21]([F:24])([F:23])[F:22])(=O)=[O:19]>ClCCl.O>[F:22][C:21]([F:24])([F:23])[S:18]([O:10][C:7]1[CH:8]=[CH:9][C:4]2[CH:3]=[CH:2][O:1][C:5]=2[CH:6]=1)(=[O:19])=[O:17]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 1288446-Hydroxybenzofuran

생성물 1

HCID 11357589Benzofuran-6-YL trifluoromethanesulfonate수율 88.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of benzofuran-6-ol (17.0 g, 127 mmol) in pyridine (20 g, 254 mmol) and dichloromethane (200 mL) was added Tf2O (53.7 g, 190 mmol). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to afford a crude product that was purified by column chromatography on silica gel (5-10% ethyl acetate in petroleum ether) to afford benzofuran-6-yl trifluoromethanesulfonate (30.0 g, 88.0% yield). 1H NMR (300 MHz, CDCl3) δ: 7.72 (d, J=2.1, 1H), 7.67 (d, J=8.7, 1H), 7.48 (d, J=1.5, 1H), 7.19 (dd, J=8.7, 2.1, 1H), 6.82-6.91 (m, 1H).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a crude product that
  7. customwas purified by column chromatography on silica gel (5-10% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-af78f512aeda49818bd7f5d2a3e725b1
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969386B2

반응 노트

불러오는 중…