Reaction #927270

Reaction equation

8-cycloprop-1-enyl-octan-2-one

triethylamine

methoxylamine hydrochloride

→

8-cycloprop-1-enyl-octan-2-one O-methyl oxime

Yield 28.4%

Solvents

methanol

Conditions

Workup

1. 1
   OtherThe ice bath was removed
2. 2
   workup.ADDITIONWater and ether were added
3. 3
   OtherThe phases were separated
4. 4
   Washthe aqueous phase was washed with ether
5. 5
   WashThe combined ether phases were washed with dilute aqueous hydrochloride acid, water (2×), and brine
6. 6
   Dryingdried over magnesium sulfate
7. 7
   Filtrationfiltered

Procedure

To a solution of 0.15 g (0.9 mmol) of 8-cycloprop-1-enyl-octan-2-one in 10 mL of methanol cooled in an ice bath was added 0.30 g (3 mmol1) of triethylamine and 0.83 g of a 30-35% aqueous solution of methoxylamine hydrochloride (3 mmol). The ice bath was removed, and the reaction mixture was stirred at room temperature for 1.5 hours. Water and ether were added. The phases were separated and the aqueous phase was washed with ether. The combined ether phases were washed with dilute aqueous hydrochloride acid, water (2×), and brine, then dried over magnesium sulfate, filtered and stripped. Column chromatography gave 50 mg of 8-cycloprop-1-enyl-octan-2-one O-methyl oxime (Compound 47) as a 30% solution in ether. The ratio of oxime isomers was 3:1.

Source