Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

HRID 73136

反応式

HRID 73136 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][Si:14]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 701194-Bromobenzyl alcohol

生成物 1

HCID 108595834-Bromobenzyloxy-tert-butyldimethylsilane収率 89.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Bromobenzyl alcohol (50.00 g, 267.3 mmol), tert.-butyldimethylsilyl chloride (52.38 g, 347.5 mmol), and imidazole (23.66 g, 347.5 mmol) were dissolved in anhydrous DMF (300 mL). This solution was allowed to stir at room temperature overnight and then poured into ice-water (600 mL). The organic layer was separated off and washed with saturated aqueous sodium bicarbonate (2×200 mL) and water (2×200 mL). We obtained colorless oil (71.9 g, 88%): 1H NMR (CDCl3): δ 0.10 (s, (CH3)2Si), 0.94 (s, (CH3)3C), 4.7 (s, CH2O), 7.20 (d, J=7.8 Hz, C6H4), 7.45 (d, J=7.8 Hz, C6H4); 13C NMR (CDCl3): δ.

後処理

  1. customThe organic layer was separated off
  2. washwashed with saturated aqueous sodium bicarbonate (2×200 mL) and water (2×200 mL)

出典と根拠

ORDレコード
ord-ec9cded50846470ea94b58b2ff5bc129
出典データセット
uspto-grants-2014_09
特許番号
US08829033B2

関連ノート

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