Klages, Friedrich published the artcileOxonium salts. II. A new reaction for the preparation of trialkyloxonium salts, Application In Synthesis of 16332-06-2, the publication is Chemische Berichte (1953), 1322-6, database is CAplus.
cf. C.A. 47, 9897f. When 122 g. di-Me etherate (I) of HSbCl6 in 100 cc. liquid SO2 is treated at -30° with 32.5 g. N2CHCO2Et (II) while the mixture is stirred in a N stream, the SO2 evaporated, and the residue triturated with ether, 97.5% trimethyloxonium hexachloroantimonate, [R3O]⊕SbCl6 symmetric difference symbol (III) (R = Me), sandlike crystals, m. 159°, is obtained. III are formed according to the reactions: R2O.HSbCl6 + II → [EtO2CCH2O⊕R2]SbCI6 symmetric difference symbol (IV) + N2; IV + R2O → EtO2CCH2OR + III. Evaporating the ether solution gives 50% MeOCH2CO2Et, b13 41-5°, b. 131° (amide, m. 92°). The di-Et homolog (48 g.) of I, treated in 100 cc. CH2Cl2 with 11.4 g. II at 10° and the residue triturated with ether gives 85% III (R = Et), m. 133°, and 2% EtOCH2CO2Et, b13 53° (amide, m. 82°). Adding dropwise 29.9 g. SbCl5 to 20.4 g. Pr2O in 100 cc. SO2 at -70° and treating the precipitate with HCl give 100% Pr homolog of I, m. 72° (sealed tube, decomposition), which, treated in CH2Cl2 with II gives 73% III (R = Pr), m. 105° (decomposition). Adding 29.9 g. SbCl5 dropwise to 26 g. Bu2O in 100 cc. SO2 while simultaneously passing HCl and N through the mixture and evaporating the SO2 give 60 g. Bu homolog of I, m. 45-54° (sealed tube, decomposition), which with II in CH2Cl2 yields 33% III (R=Bu), m. 119° (decomposition). Saturating 60 g. SbCl5 in 50 cc. CH2Cl2 at -70° with dry HCl in a Natm. and then adding very slowly 41 g. (Me2CH)2O (the mixture must not turn red) give 87% Me2CH homolog (V) of I, m. 104°(decomposition). Adding 15.2 g. II dropwise to 72 g. V in 200 cc. CH2Cl2 at -5° and treating the precipitate repeatedly in CH2Cl2with II gives 9% [EtO2CCH2O(CHMe2)2]⊕SbCl6 symmetric difference symbol, m. 116° (decomposition); di-iso-Am homolog, 5%, m. 89° (decomposition).
Chemische Berichte published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Application In Synthesis of 16332-06-2.
Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem