Imidazole → ((4-Bromo-2-methoxybenzyl)oxy)(tert-butyl)dimethylsilane

HRID 1888459ノート

反応式

HRID 1888459 の反応式
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[C:12]([O:18][CH3:19])[CH:11]=1.N1C=CN=C1>CN(C=O)C>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][O:17][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[C:12]([O:18][CH3:19])[CH:11]=1

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 151282434-Bromo-2-methoxybenzyl alcohol

生成物 1

HCID 18687376((4-Bromo-2-methoxybenzyl)oxy)(tert-butyl)dimethylsilane収率 98%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

tert-Butyldimethylsilyl chloride (1.04 g, 6.9 mmol) was added to a mixture of (4-bromo-2-methoxyphenyl)methanol (1.0 g, 4.6 mol) and imidazole (470 mg, 7.0 mmol) in DMF (15 mL) and the resultant mixture was stirred at ambient temperature for 66 h. The mixture was concentrated to about a third of the original volume then diluted with water and extracted with diethyl ether (×3). The combined organic layer was dried over magnesium sulfate, filtered and evaporated. The resultant residue was purified by chromatography (silica, 50 g column, Si-SPE, 5% diethyl ether in pentane) to afford the title compound as a colourless oil (1.51 g, 98%). 1H NMR (CDCl3, 400 MHz): 7.34 (dt, J=8.1, 1.05 Hz, 1H); 7.11 (dd, J=8.1, 1.8 Hz, 1H); 6.95 (d, J=1.8 Hz, 1H); 4.69 (d, J=1.0 Hz, 2H); 3.81 (s, 3H); 0.97-0.94 (m, 9H); 0.13-0.08 (m, 6H).

後処理

  1. concentrationThe mixture was concentrated to about a third of the original volume
  2. additionthen diluted with water
  3. extractionextracted with diethyl ether (×3)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resultant residue was purified by chromatography (silica, 50 g column, Si-SPE, 5% diethyl ether in pentane)

出典と根拠

ORDレコード
ord-314efdb7205a43e98f10d5efb3d51ab3
出典データセット
uspto-grants-2013_08
特許番号
US08501765B2

反応ノート

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