Hydroxylamine → HCID 14208182, Verbindung

A solution of 0.2 g (2.2 mmol) of dimethylamino-ethanol and 0.4 g (2.3 mmol) of dry p-toluenesulphonic acid in 50 ml of dry carbon tetrachloride was stirred at room temperature until all the amino-alcohol had been converted into its ammonium tosylate salt as determined by thin layer chromatography (chloroform:methanol 80:20 by volume). Then 0.5 g (2.mmol) of 2-tridecyl-2,3-dihydrofuran was added and the mixture was stirred in the same conditions until complete reaction of the dihydro compound as determined by TLC (petroleum ether:ether 90:10 by volume). After evacuation of the solvent under reduced pressure, the residue was diluted by 20 ml of a saturated aqueous sodium carbonate solution and extracted several times with diethyl ether. The diethyl ether phase was washed with water until neutrality, dried on anhydrous magnesium sulphate and filtered. The residue, after evaporation of water, was chromatographed on silica gel using successively mixtures of methanol:chloroform, from 1:99 to 20:80 by volume, to yield 0.5 g of the cis-trans title compound as an oil. NMR (80 MHz, CDCl3, HMDS*) δ 0.82 (t, 3H, CH3 alkyl chain) 1.17 (large s, 22H, (CH2)11) 1.92 (m, 4 H, CH2 --C--O) 2.17 (s, 6H, CH3N) 2.42 (m, 4H, CH2N+ ##STR10## 3.25-3.87 (m, 2H, CH2O) 3.92 (m, 1H, CH--O) 4.95 (m, 1H, ##STR11##

1. extractionextracted several times with diethyl ether
2. washThe diethyl ether phase was washed with water until neutrality
3. dry with materialdried on anhydrous magnesium sulphate
4. filtrationfiltered
5. customThe residue, after evaporation of water
6. customwas chromatographed on silica gel using successively mixtures of methanol

ORD-Eintrag

ord-a9b7590c5b8042f984ed4a30cc565128

Quelldatensatz

uspto-grants-1989_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04888337