Diisopropylethylamine → 2-Chloro-6-(2-(trimethylsilanyl)ethoxymethoxymethyl)pyridine

HRID 376281

Reaction equation

HRID 376281 reaction equation
ClCC([Si](C)(C)C)[CH2:4][O:5][CH2:6][CH:7]([Si:10]([CH3:13])([CH3:12])[CH3:11])CCl.[Cl:18][C:19]1[N:24]=[C:23]([CH2:25][OH:26])[CH:22]=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]([CH2:25][O:26][CH2:4][O:5][CH2:6][CH2:7][Si:10]([CH3:11])([CH3:12])[CH3:13])[N:24]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 182139(6-Chloropyridin-2-yl)methanolHCID 57232046HCID 57232046, compound

Product 1

HCID 108022522-Chloro-6-(2-(trimethylsilanyl)ethoxymethoxymethyl)pyridineYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3.20 ml of chloromethyl-2-(trimethylsilyl)ethyl ether (18.2 mmol) are added dropwise to a solution containing 2.50 g of (6-chloropyridin-2-yl)methanol (17.4 mmol), 3.30 ml of diisopropylethylamine (19.1 mmol) and 20 ml of dichloromethane cooled to 0° C. maintained under a nitrogen atmosphere. The mixture is stirred for 3 hours at room temperature and then the dichloromethane is evaporated off, the residue is taken up in water, the mixture is extracted with diethyl ether, the organic phase is washed with water and then dried over sodium sulfate. After filtration and evaporation of the solvent, the title product is isolated by chromatography on a silica column (eluent: dichloromethane).

Workup

  1. temperaturemaintained under a nitrogen atmosphere
  2. customthe dichloromethane is evaporated off
  3. extractionthe mixture is extracted with diethyl ether
  4. washthe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-33e28e9b139c4391b28bbb1113071079
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Linked notes

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