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Water → 3-[4-(4-Bromophenoxy)-3-(tert-butyldimethylsilanyloxy)-5-methylhexyl]pyridine

HRID 380022
ノート
印刷プレビュー

反応式

HRID 380022 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:30]=[CH:29][C:13]([O:14][C@@H:15]([CH:26]([CH3:28])[CH3:27])[C@H:16]([OH:25])[CH2:17][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:12][CH:11]=1.O.CCOCC>CN(C)C=O>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH:15]([CH:26]([CH3:27])[CH3:28])[CH:16]([O:25][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:17][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[CH:29][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 57267460(3S,4R)-3-(4-bromophenyloxy)-2-methyl-6-(3-pyridyl)hexan-4-ol

生成物 1

HCID 183675413-[4-(4-Bromophenoxy)-3-(tert-butyldimethylsilanyloxy)-5-methylhexyl]pyridine収率 57.3%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

Solid tert-butyldimethylsilyl chloride (0.46 g) was added to a solution of (3R, 4S)-4-(4-bromophenoxy)-5-methyl-1-pyridin-3-yl-3-hexanol (0.93 g) andimidazole (0.26 g) in dry dimethylformamide (12 ml) and the resulting solution stirred at room temperature for 3 days. Water (100 ml) and ether (100 ml) were added. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluting with dichloromethane then dichloromethane: hexane (1:1) to give the sub-title compound as an oil (0.70 g).

後処理

  1. customThe organic phase was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel eluting with dichloromethane

出典と根拠

ORDレコード
ord-ac4821aca9a346fbbe3bb53eb25278d3
出典データセット
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06300352B1

反応ノート

読み込み中…

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