Tetrahydrofuran → HCID 21670486, compound

Participants

Reaction Conditions

Reaction Steps

6.91 g of potassium carbonate and 8.75 g of tetra-butylammonium hydrogensulphate are successively added to a solution of 7.1 g of 2,6-pyridinedimethanol in 100 cm3 of tetrahydrofuran. The reaction mixture is cooled to 20° C. in an ice bath and 6.60 g of potassium hydroxide are then added, while maintaining the temperature of the reaction mixture at 30° C. After stirring for 15 minutes at this temperature, a solution of 4.73 cm3 of 2-bromoethyl methyl ether in 10 cm3 of tetrahydrofuran is added over approximately 15 minutes. The reaction mixture is stirred for 12 hours at 20° C. and a solution of 4.73 cm3 of 2-bromoethyl methyl ether in 10 cm3 of tetrahydrofuran is then added over 15 minutes. The reaction mixture is stirred for 48 hours at 20° C. The white suspension obtained is filtered. The solid is rinsed with 750 cm3 in total of tetrahydrofuran. The combined filtrates are concentrated under reduced pressure (2.7 kPa) at 40° C. The residual oil obtained (18 g) is purified by chromatography on a column of silica (0.020-0.045 mm), eluting with an ethyl acetate/methanol mixture (9:1 by volume), collecting 50 cm3 fractions). The fractions containing the expected product are combined and concentrated under reduced pressure (2.7 kPa) at 50° C. The oil obtained (1.6 g) is dissolved in 12 cm3 of distilled water and the solution is filtered. After freeze-drying, 1.52 g of 2,6-bis(2-methoxyethyloxymethyl)pyridine are obtained in the form of a fluid yellow oil [1H NMR spectrum (400 MHz, (CD3)2SO-d6, δ in ppm): 3.29 (s, 6H: 2×OCH3); 3.53 and 3.66 (2 mts, 4H each: OCH2CH2O); 4.57 (s, 4H: 2×ArCH2O); 7.35 (d, J=8 Hz, 2H: ═CH at 3 and ═CH at 5); 7.83 (t, J=8 Hz, 1H: ═CH at 4)].

Provenance & Evidence