Triethylamine → HCID 20349680, compound

HRID 1449416Notes

Reaction equation

HRID 1449416 reaction equation
S([O-])(O)(=O)=[O:2].[C:6]([C:10]1[S:11][S+:12]=[CH:13][C:14]=1[CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:9])([CH3:8])[CH3:7].C(N([CH2:25][CH3:26])CC)C>C(O)C>[CH2:25]([O:2][C:10]1([C:6]([CH3:9])([CH3:8])[CH3:7])[C:14]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:13][S:12][S:11]1)[CH3:26]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86736849HCID 86736849, compound

Product 1

HCID 20349680HCID 20349680, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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).

Workup

  1. customThe solvent was removed under diminished pressure
  2. extractionthe residue extracted with ether
  3. filtrationThe ethereal solution was filtered
  4. distillationdistilled under diminished pressure
  5. customto remove the ether

Sources & evidence

ORD record
ord-0e6744b6ad5841be82fcd3e2e7793f6a
Source dataset
uspto-grants-1980_02
Patent number
US04190727

Reaction notes

Loading…