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Imidazole → (3RS,4S)-3-[4-(4-Bromophenoxy)-3-(tertbutyldimethylsilanyloxy)pentyl]pyridine

HRID 379970
Notes
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Reaction equation

HRID 379970 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C@@H:7]([CH3:18])[CH:8]([OH:17])[CH2:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:3]=1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C@@H:7]([CH3:18])[CH:8]([O:17][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:9][CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:19][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57000220(2S,3RS)-2-(4-Bromophenoxy)-5-pyridin-3-ylpentan-3-ol

Product 1

HCID 20692755(3RS,4S)-3-[4-(4-Bromophenoxy)-3-(tertbutyldimethylsilanyloxy)pentyl]pyridineYield 94%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

To a solution of (3RS,4S)-4-(4-Bromophenoxy)-1-pyridin-3-yl-pentan-3-ol (2.0 g, Example 4d)) in dry dichloromethane (50 ml) was added tert-butyldimethylsilyl chloride (1.17 g) and imidazole (1.08 g) and the resulting solution stirred for 24 hours, concentrated and the residue purified by chromatography on silica gel eluting with ethyl acetate:hexane (1:4 to 1:1) to afford the sub-title compound as an oil (2.52 g).

Workup

  1. concentrationconcentrated
  2. customthe residue purified by chromatography on silica gel eluting with ethyl acetate:hexane (1:4 to 1:1)

Sources & evidence

ORD record
ord-613716198e9246a0809c44cb3f41c1f2
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06300352B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes