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

HRID 75223

反応式

HRID 75223 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f65339ddf077486e98d8dcd9eb97b4d8
出典データセット
uspto-grants-2014_09
特許番号
US08835423B2

関連ノート

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