Triethylamine → 4-(Tert-butyldimethylsilyloxyethyl)-pyridine

HRID 496616Notes

Reaction equation

HRID 496616 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>C(Cl)Cl>[Si:17]([O:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 729214-Pyridineethanol

Product 1

HCID 223216194-(Tert-butyldimethylsilyloxyethyl)-pyridineYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

4-(2-Hydroxyethyl)pyridine (8.1 g, 65.8 mmol) and triethylamine (10.1 mL, 66 mmol) were dissolved in CH2Cl2 (100 mL) and cooled to −78° C. To this solution, tert-butyldimethylsilyl chloride (11.0 g, 66 mmol) was added. The mixture was allowed to warm to room temperature overnight. The mixture was placed directly on a bed of SiO2 and eluted with 100:0-10:1 CH2Cl2 methanol to provide 4-[2-(tert-Butyldimethylsilyloxy)ethyl]pyridine (15.3 g, 97%).

Workup

  1. temperatureto warm to room temperature overnight
  2. washeluted with 100:0-10:1 CH2Cl2 methanol

Sources & evidence

ORD record
ord-7fc0e9c73d9941a59af537f2574ca010
Source dataset
uspto-grants-2005_09
Patent number
US06946467B2

Reaction notes

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