Butanal → 4-Oximino-2-propyl-5-methyl-1,3-oxathiolane

Participants

Reaction Steps

1-Methyl-2-nitroethyl-1'-acetylthiobutyl ether was prepared using procedures similar to those described in Examples I and II by chloroalkylation of 1-nitro-2-propanol with n-butyraldehyde and hydrogen chloride followed by treatment of the intermediate chlorobutyl ether with thiolacetic acid and then pyridine. Treatment of this nitroalkylacylthio ether in toluene with ethanolic sodium hydroxide as described in Example I afforded crude 4- oximino-2-propyl-5-methyl-1,3-oxathiolane comprised of a mixture of Isomer A (NMR data suggests Trans Isomer) and Isomer B (NMR suggests Cis). Trituration of 26 grams of the crude oxime mixture with 150 ml of hexane and filtration afforded 3.0 grams pure Isomer A, mp 86°-88°.

Provenance & Evidence