Hydroxyamine hydrochloride → 4-Carbomethoxy-3-keto-2-methyltetrahydrothiophene oxime
Reaction equation
[C:1]([CH:5]1[CH2:9][S:8][CH:7]([CH3:10])[C:6]1=O)([O:3][CH3:4])=[O:2].Cl.[NH2:13][OH:14]>N1C=CC=CC=1>[C:1]([CH:5]1[CH2:9][S:8][CH:7]([CH3:10])[C:6]1=[N:13][OH:14])([O:3][CH3:4])=[O:2]Participants
4
Procedure
A solution of 37.26 g. (0.214 mole) of 4-carbomethoxy-3-keto-2-methyltetrahydrothiophene in 100 ml. anhydrous pyridine was treated with 18.0 g. (0.261 mole) hydroxylamine hydrochloride. The mixture was stirred 24 hours at 25°. The reaction was concentrated and partitioned between 1 N hydrochloric acid/methylene chloride. The aqueous phase was extracted two times with methylene chloride. The combined organic extracts were dried and evaporated to yield 40.1 g (99%) of pure 4-carbomethoxy-3-keto-2-methyltetrahydrothiophene oxime as a colorless oil.