Reaction #1536602

Reaction equation

ammonia

4-neopentyl-3-tertiarybutyl 1,2-dithiolium hydrogen sulfate

ethanol

ammonia

→

3-ethoxy-3-t-butyl-4-neopentyl 1,2-dithiole

Yield 61.0%

Conditions

Workup

1. 1
   OtherDuring the reaction
2. 2
   Otherwas kept at a temperature below 18° C
3. 3
   OtherThe solid, which precipitated during the reaction
4. 4
   Filtrationwas filtered off
5. 5
   OtherAfter removal of the ethanol from the filtrate under diminished pressure

Procedure

Into a mixture of 32 grams of Example 1B, i.e., 4-neopentyl-3-tertiarybutyl 1,2-dithiolium hydrogen sulfate, and 300 cc of ethanol was introduced dry ammonia gas until the mixture was saturated. During the reaction, the mixture was kept at a temperature below 18° C. After the introduction of ammonia gas was completed, the mixture was stirred for an additional hour at room temperature. The solid, which precipitated during the reaction, was filtered off. After removal of the ethanol from the filtrate under diminished pressure, there was isolated 16.5 grams (61% of theory) of 3-ethoxy-3-t-butyl-4-neopentyl 1,2-dithiole.

Source