Reaction #1536598

Reaction equation

3-tert-butyl-4-neopentyl-1,2 dithiolium hydrogen sulfate

triethylamine

→

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

Yield 77.3%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThe solvent was removed under diminished pressure
2. 2
   Extractionthe residue extracted with ether
3. 3
   FiltrationThe ethereal solution was filtered
4. 4
   workup.DISTILLATIONdistilled under diminished pressure
5. 5
   Otherto remove the ether

Procedure

To a sample of 25 grams of the product prepared in Example 1B, i.e., 3-tert-butyl-4-neopentyl-1,2 dithiolium hydrogen sulfate, in 130 grams of ethanol was added 8.5 grams of triethylamine. The mixture was stirred for 15 minutes. The solvent was removed under diminished pressure and the residue extracted with ether. The ethereal solution was filtered and distilled under diminished pressure to remove the ether. There was isolated 17.1 grams (77.3% of theory) of 3-ethoxy-3-t-butyl-4-neopentyl 1,2-dithiole as an oil; n.m.r. (CCl4) τ in ppm, 3.81, 1H singlet (vinyl); 6.50 and 6.56, 2H two quartets (diastereotopic, J=7 cps, ethoxy); 7.22, 1H doublet (diastereotopic, J=15 cps. neopentyl proton); 7.82, 1H doublet (diastereotopic, J=15 cps neopentyl proton); 8.62, 9H singlet (t-butyl); 8.83, 3H triplet (J=7 cps, ethoxy); and 8.96, 9H singlet (t-butyl).

Source