Water → 4-(Tert-butyldimethylsilyloxyethyl)-pyridine

HRID 2420990Notes

Reaction equation

HRID 2420990 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.N1C(C)=CC=CC=1C.Cl[Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].O>ClCCl>[O:1]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)[Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 79372,6-LutidineHCID 28928tert-Butyldimethylsilyl chlorideHCID 729214-Pyridineethanol

Product 1

HCID 223216194-(Tert-butyldimethylsilyloxyethyl)-pyridineYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercially available 4-(2-hydroxyethyl)pyridine (10.0 g, 81.2 mmol) was dissolved in dichloromethane (400 mL), then 2,6-lutidine (26.1 g, 244 mmol) and chloro-tert-butyldimethylsilane (32.0 g, 121 mmol) were added thereto, followed by stirring at room temperature for 3 hours. After completion of the reaction was confirmed by thin-layer chromatography, water was added to the reaction mixture, and the resulting mixture was separated into organic layer and aqueous layer. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure to give 4-[2-(tert-butyldimethylsiloxy)ethyl]pyridine (19.2 g, quantitative yield).

Workup

  1. additionwas added to the reaction mixture
  2. customthe resulting mixture was separated into organic layer and aqueous layer
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9d60476223354b81bf4b787fd76a5c4b
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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