Reaction #947

Reaction equation

Chlorosulphonic acid

product

(+-)-2-Amino-2-ethylhex-4-en-1-ol

→

desired product

Yield 57.0%

(+-)-2-But-2-enyl-2-ethylaziridine

Yield 57.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   workup.ADDITIONWhen addition
2. 2
   FiltrationThe resulting crystals were filtered off
3. 3
   Washwashed with acetonitrile/pet. ether
4. 4
   Otherdried
5. 5
   workup.ADDITIONtaken up in a mixture of 50%
6. 6
   workup.DISTILLATIONKOH (100 mL) and water (55 mL) and distilled over KOH

Procedure

Chlorosulphonic acid (18 mL) was added to a solution of the product from step (e) (32.3 g) in acetonitrile (100 ml) at least 9° C. When addition was complete, the mixture was warmed to room temperature. The resulting crystals were filtered off, washed with acetonitrile/pet. ether, dried, taken up in a mixture of 50% w/v aqu. KOH (100 mL) and water (55 mL) and distilled over KOH to give the desired product as a colourless oil (16.1 g). 1H NMR consistent with the proposed structure.

Source