Methanol → HCID 20349688, compound

HRID 1449415Notes

Reaction equation

HRID 1449415 reaction equation
Cl([O-])(=O)(=O)=O.[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].[CH3:20][OH:21]>C(N(CC)CC)C>[CH3:20][O:21][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

Participants

4

Reactant 2

HCID 887MethanolHCID 20349678HCID 20349678, compound

Product 1

HCID 20349688HCID 20349688, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a sample of 136.8 grams of the product prepared as described in Example 2B, i.e., 3-tert-butyl-4-neopentyl-1,2-dithiolium perchlorate, and 180 grams of methanol was added over a 10 minute period 44 grams of triethylamine. The mixture was stirred for 20 minutes. The solvent was removed under diminished pressure and the residue taken up in ether and water. The etheral solution was washed two times with water, dried over anhydrous magnesium sulfate, filtered and distilled under diminished pressure to remove the ether. The product, 3-methoxy-3-tertiarybutyl-4-neopentyl 1,2-dithiole, was isolated as 96 grams (88.8% of theory) of an oil, n.m.r. (CCl4) τ in ppm, 3.81, 1H singlet (vinyl); 6.81, 3H singlet (methoxy); 7.23, 1H doublet (diastereotopic, J=15 cps, neopentyl proton); 7.82, 1H doublet (diastereotopic, J=15 cps, neopentyl proton); 8.63, 9H singlet (t-butyl) and 8.97, 9H singlet (t-butyl).

Workup

  1. customThe solvent was removed under diminished pressure
  2. washThe etheral solution was washed two times with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationdistilled under diminished pressure
  6. customto remove the ether

Sources & evidence

ORD record
ord-0e83897eab7d4e018a85218628d42f4d
Source dataset
uspto-grants-1980_02
Patent number
US04190727

Reaction notes

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