2,6-Lutidine → [(3,5-Dichlorobenzyl)oxy](triisopropyl)silane

HRID 75223

반응식

HRID 75223 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C(C)=CC=CC=1C.O([Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])S(C(F)(F)F)(=O)=O>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Cl:8])[CH:7]=1)[CH2:9][O:10][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29]

참가 물질

6

반응물 3

HCID 79372,6-LutidineHCID 432363,5-Dichlorobenzylic alcoholHCID 2724529Triisopropylsilyl trifluoromethanesulfonate

생성물 1

HCID 11739096[(3,5-Dichlorobenzyl)oxy](triisopropyl)silane수율 79%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of (3,5-dichlorophenyl)methanol (10.0 g, 56.5 mmol) in methylene chloride (100 mL) at 0° C. was added 2,6-lutidine (16.4 mL, 141 mmol) followed by triisopropylsilyl triflate (19.7 mL, 73.4 mmol), and was stirred at 0° C. for 2 hours. The reaction was diluted with water and the organic layer was separated, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography on silica gel, eluting with hexane to provide the desired product (14.8 g, 79%). LC/MS: 333 (M+H)+, 1H NMR (CDCl3) δ 7.23 (s, 3H), 4.78 (s, 2H), 1.18 (m, 3H), 1.03 (s, 18H).

후처리

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with hexane

출처 및 근거

ORD 기록
ord-f65339ddf077486e98d8dcd9eb97b4d8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835423B2

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