Isopropanol → HCID 20349691, compound

HRID 1449419Notes

Reaction equation

HRID 1449419 reaction equation
Cl(O)(=O)(=O)=O.[CH2:6]([C:11]1[CH:12]([C:16]([CH3:19])([CH3:18])[CH3:17])[S:13][S:14][CH:15]=1)[C:7]([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C.[CH:27]([OH:30])([CH3:29])[CH3:28]>>[CH:27]([O:30][C:12]1([C:16]([CH3:19])([CH3:18])[CH3:17])[C:11]([CH2:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[CH:15][S:14][S:13]1)([CH3:29])[CH3:28]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 8471TriethylamineHCID 86736850HCID 86736850, compound

Product 1

HCID 20349691HCID 20349691, compoundYield 98%

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).

Workup

  1. customThe excess of isopropanol was removed by distillation under diminished pressure
  2. dissolutionThe residue was dissolved in ether
  3. filtrationthe ethereal solution was filtered
  4. customThe ethereal solution was evaporated under diminished pressure

Sources & evidence

ORD record
ord-ce32893f45094133ba994ef1c6561a9f
Source dataset
uspto-grants-1980_02
Patent number
US04190727

Reaction notes

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