Cyclopropanol, 1-ethoxy

CYCLOPROP AH ONE ETHYL (CHIACETAL FROM ETHYL 3-CHLDR0PR0PAH0ATE (Cyclopropanol, 1-ethoxy-)... 

Methylmagnesium bromide Magnesium, bromomethyl- (8,9) (75-16-1) Diisopropylamine (8) 2-Propanamine, N-(l-methylethyl)- (9) (108-18-9) 2-Methyi-i-tetralone 1 (2H)-Naphthalenone, 3,4-dihydro-2-methyl- (8,9) (1590-08-5) Cyclopropanone ethyl hemiketal Cyclopropanol, 1-ethoxy- (8.9) (13837-45-1) Sodium hydride (8,9) (7646-69-7)... 

Cyclopropanone ethyl hemiacetal Cyclopropanol, 1-ethoxy- (8,9) (13837-45-1) l-Ethoxy-l-tr1methyls1loxycyclopropane Silane, [(l-ethoxycyclopropyl)oxy)-trimethyl- (8,9) (27374-25-0)... 

Cyclopropanol, 1-amino- (8, 9), hydrochloride (58939-46-1) Cyclopropylamine, 1-ethoxy- (8) Cyclopropanamine, 1-ethoxy-(9), hydrochloride (58939-48-3)... 

Upon treatment with lithium aluminum hydride, cyclopropanones are reduced to cyclopropanols, e.g., 18- -156. 1-Ethoxy cyclopropyl... 

With the exception of a few cyclopropanone hemiacetals, which are readily reduced with lithium aluminum hydride in diethyl ether to give the corresponding cyclopropanols, conversion of a cyclopropyl-oxygen bond to a cyclopropyl-hydrogen bond has only been achieved by reductive dealkoxylation of 1-alkoxycyclopropylamines where the alkoxy group is either methoxy or ethoxy 3. The reductions can be carried out with various hydrides, but the optimum reaction conditions in a specific case depend on the structure of the substrate. 

In addition to cyclopropanones, their hemiacetals have also been used in reductions with complex metal hydrides. The reaction of 1-ethoxycyclopropanol (7) with lithium aluminum hydride in diethyl ether gave cyclopropanol in 45% yield,while l-ethoxy-2-methylcyclopropanol (9, mixture of stereoisomers) afforded cis- and irau -2-methylcyclopropanol (10) in a ratio of 79 21. The isomers 10 were separated by preparative HPLC. ... 

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