Imidazole → (2-Allyl-3-bromo-6-chloro-5-(4-methoxybenzyl)phenoxy)(tert-butyl)dimethylsilane

HRID 2206774ノート

反応式

HRID 2206774 の反応式
[CH2:1]([C:4]1[C:9]([Br:10])=[CH:8][C:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:6]([Cl:20])[C:5]=1[OH:21])[CH:2]=[CH2:3].[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].N1C=CN=C1>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:1]([C:4]1[C:9]([Br:10])=[CH:8][C:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:6]([Cl:20])[C:5]=1[O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:2]=[CH2:3]

参加物

6

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 867140802-Allyl-3-bromo-6-chloro-5-(4-methoxybenzyl)phenol

生成物 1

HCID 86714082(2-Allyl-3-bromo-6-chloro-5-(4-methoxybenzyl)phenoxy)(tert-butyl)dimethylsilane収率 86%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of phenol 185 (2.29 g, 6.23 mmol) in DMF (30 mL) were added tert-butyldimethylsilyl chloride (1M in THF, 9.35 mL, 9.35 mmol), imidazole (1.3 g, 18.7 mmol) and catalytic DMAP. The mixture was stirred at 50° C. for 15 hours. The mixture was extracted with EtOAc/aq. 50% NaCl solution (100 mL/500 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 186 (2.57 g, 86%).

後処理

  1. extractionThe mixture was extracted with EtOAc/aq
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-1edccaa93537468abcb64d3e613c7bec
出典データセット
uspto-grants-2016_06
特許番号
US09371303B2

反応ノート

読み込み中…