Ethanethiol → 5-[Bis(ethylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 464408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 464408
CS[C:3]([S:14][CH3:15])=[C:4]1[C:9](=[O:10])[O:8][C:7]([CH3:12])([CH3:11])[O:6][C:5]1=[O:13].[CH2:16]([SH:18])[CH3:17].[CH3:19][O-].[Na+]>CO>[CH2:16]([S:18][C:3]([S:14][CH2:15][CH3:19])=[C:4]1[C:9](=[O:10])[O:8][C:7]([CH3:12])([CH3:11])[O:6][C:5]1=[O:13])[CH3:17]

Komponenten

5

Edukt 3

HCID 6343EthanethiolHCID 17451285-[Bis(methylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 10942334Sodium Methoxide

Produkt 1

HCID 136798125-[Bis(ethylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dioneAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 5-[bis(methylthio)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione (2.3 g, 9.2 mmole, described in example 3), ethanethiol (8.4 g, 10 mL, 135 mmole) and sodium methoxide (480 mg, 20.7 mmole) in dry methanol (12 mL) was stirred at 20°-22° C. for 30 min. The solution was poured into ice water. The resultant mixture was extracted with ethyl acetate. The combined extracts were washed with water, dried (MgSO4) and concentrated to dryness under reduced pressure. The residue was purified by HPLC (20% ethyl acetate in hexane, v/v). The purest fractions were combined. The solvent was removed under reduced pressure to give 0.59 g of the title compound as an oil; NMR (CDCl3) δ 1.36 (t, J=7 Hz, 6H), 1.72 (s, 6H), 3.11 (3t, J=7 Hz, 4H); IR (CHCl3) 1715 cm-1 ; UVλmax (MeOH) 345 nm (ε 13,040), 215 (8160).

Aufarbeitung

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. washThe combined extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was purified by HPLC (20% ethyl acetate in hexane, v/v)
  6. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1e286971a61643f58f9db9924f333c58
Quelldatensatz
uspto-grants-1985_10
Patentnummer
US04547516

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