Methanol → HCID 86702161, compound

HRID 1776238Notes

Reaction equation

HRID 1776238 reaction equation
[CH3:1][C:2]([N:6]1[CH2:10][CH2:9][CH2:8][S:7]1(=[O:12])=[O:11])([C:4]#[CH:5])[CH3:3].C[OH:14]>S(=O)(=O)(O)O.[Hg]=O>[O:11]=[S:7]1(=[O:12])[CH2:8][CH2:9][CH2:10][N:6]1[C:2]([CH3:1])([CH3:3])[C:4](=[O:14])[CH3:5]

Participants

5

Reactant 2

HCID 887MethanolHCID 64005706HCID 64005706, compound

Product 1

HCID 86702161HCID 86702161, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(2-methylbut-3-yn-2-yl)isothiazolidine-1,1-dioxide (3.500 g, 18.7 mmol) and mercury(II) oxide (0.810 g, 3.7 mmol) in methanol (100 mL) and 2 N aqueous sulfuric acid (50 mL) was heated at 90° C. for 3 hrs. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo. The residue was treated with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) to afford the desired product as a yellow oil (1.65 g, 43%). 1H NMR (300 MHz, CDCl3) δ 3.38 (t, 2H, J=6.6 Hz), 3.21 (t, 2H, J=7.5 Hz), 2.42-2.30 (m, 2H), 2.28 (s, 3H), 1.60 (s, 6H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. additionThe residue was treated with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried (anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c32f8fc8928346cb9b18d9a753470274
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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