Methanol → HCID 86702161, Verbindung

HRID 1776238Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776238
[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]

Komponenten

5

Edukt 2

HCID 887MethanolHCID 64005706HCID 64005706, Verbindung

Produkt 1

HCID 86702161HCID 86702161, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30856Mercuric oxideKatalysatorHCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c32f8fc8928346cb9b18d9a753470274
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265772B2

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