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

HRID 380022
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HRID 380022 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ac4821aca9a346fbbe3bb53eb25278d3
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06300352B1

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