Reaction #1536601

Reaction equation

isopropanol

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

triethylamine

→

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

Yield 98.0%

Conditions

Workup

1. 1
   OtherThe excess of isopropanol was removed by distillation under diminished pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ether
3. 3
   Filtrationthe ethereal solution was filtered
4. 4
   OtherThe ethereal solution was evaporated under diminished pressure

Procedure

To a sample of 5 grams of Example 2B, i.e., 4-neopentyl-3-t-butyl 1,2 dithiole perchlorate, in 50 grams of isopropanol was added 2.5 grams of triethylamine. The excess of isopropanol was removed by distillation under diminished pressure. The residue was dissolved in ether and the ethereal solution was filtered. The ethereal solution was evaporated under diminished pressure to yield 4.3 grams (98% of theory) of 3-isopropoxy-3-t-butyl-4-neopentyl 1,2 dithiole; n.m.r. (CCl4) in ppm, 3.97, 1H singlet (vinyl); 6.18 1H multiplet (isopropoxy); 7.17, 1H doublet (diastereotopic, J=15 cps, neopentyl; 7.88, 1H doublet (diastereotopic, J=15 cps, neopentyl); 8.62, 9H singlet (t-butyl); 8.83, 6H doublet (isopropoxy); and 8.91, 9H singlet (t-butyl).

Source