2,6-Lutidine → (3,5-Dichlorophenoxy)tris(propan-2-YL)silane

HRID 75238

반응식

HRID 75238 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C(C)=CC=CC=1C.O([Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])S(C(F)(F)F)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:8])[CH:7]=1)[O:9][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28]

참가 물질

5

반응물 3

HCID 79372,6-LutidineHCID 115713,5-DichlorophenolHCID 2724529Triisopropylsilyl trifluoromethanesulfonate

생성물 1

HCID 21594466(3,5-Dichlorophenoxy)tris(propan-2-YL)silane수율 91.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of 3,5-dichloro-phenol (5.9 g, 36 mmol) in methylene chloride (50 mL,) was added 2,6-lutidine (8.38 mL, 72.4 mmol) and triisopropylsilyl triflate (9.7 mL, 36 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 4 h. The reaction was quenched with 0.1 N HCl and diluted with ethyl acetate. The organic solution was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified with flash chromatography (5% ethyl acetate/hexanes) to give the desired product as a colorless oil (10.5 g, 91%). 1H NMR (400 MHz, CDCl3): δ 6.95 (t, J=1.8 Hz, 1 H), 6.76 (d, J=1.8 Hz, 2 H), 1.26 (m, 3 H), 1.09 (d, J=7.0 Hz, 18 H).

후처리

  1. customThe reaction was quenched with 0.1 N HCl
  2. additiondiluted with ethyl acetate
  3. washThe organic solution was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with flash chromatography (5% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-1d1d219f150d49b980fe0b4cfd8300ce
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835423B2

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