Imidazole → HCID 20519039、化合物

HRID 1644215ノート

反応式

HRID 1644215 の反応式
N1C=CN=C1.[Br:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([OH:17])=[CH:9][CH:8]=1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Br:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5756094-Bromonaphthalen-1-ol

生成物 1

HCID 20519039HCID 20519039、化合物収率 86.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of imidazole (2.3 g, 34 mmole) and 4-bromonaphthol (13, 5.0 g, 22 mmole) in DMF (10 mL) at 0° C. was added t-butyldimethylsilyl chloride (3.7 g, 24.6 mmole) in several portions. The mixture was warmed to room temperature and stirred for 2 h. The reaction mixture was partitioned between Et2O (500 mL) and water (300 mL) and the aqueous layer was back-extracted with Et2O (300 mL). The combined organic layers were washed with water (300 mL) and brine (300 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (silica gel, hexanes) to afford (4-bromonaphthalen-1-yloxy)(tert-butyl)dimethylsilane (14, 6.4 g, 85%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.21 8.14 (m, 2H), 7.61-7.49 (m, 3H), 6.74 (d, J=8.2 Hz, 1H), 1.10 (s, 9H), 0.28 (s, 6H).

後処理

  1. customThe reaction mixture was partitioned between Et2O (500 mL) and water (300 mL)
  2. extractionthe aqueous layer was back-extracted with Et2O (300 mL)
  3. washThe combined organic layers were washed with water (300 mL) and brine (300 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel, hexanes)

出典と根拠

ORDレコード
ord-a8d4ed57a9bc4790b560056c943de546
出典データセット
uspto-grants-2012_02
特許番号
US08124607B2

反応ノート

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