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

HRID 380022Notes

Reaction equation

HRID 380022 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ac4821aca9a346fbbe3bb53eb25278d3
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

Loading…