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

HRID 376281Notes

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

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

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

Sources & evidence

ORD record: ord-33e28e9b139c4391b28bbb1113071079
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06020345

Reaction notes

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