Ethanethiol → 5-[(Ethylthio)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 464406Notes

Reaction equation

HRID 464406 reaction equation
CO[CH:3]=[C:4]1[C:9](=[O:10])[O:8][C:7]([CH3:12])([CH3:11])[O:6][C:5]1=[O:13].[CH2:14]([SH:16])[CH3:15]>C(O)C>[CH2:14]([S:16][CH:3]=[C:4]1[C:5](=[O:13])[O:6][C:7]([CH3:11])([CH3:12])[O:8][C:9]1=[O:10])[CH3:15]

Participants

4

Reactant 2

HCID 6343EthanethiolHCID 1521115-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 135057595-[(Ethylthio)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dioneYield 60.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (7 g, 38 mmole), described by Bihlmayer et al., supra, was suspended in ethanol (70 ml). The suspension was stirred vigorously while being subjected to the addition of ethanethiol (12.85 g, 200 mmole). The mixture was heated at reflux until all the starting material had been consumed, as indicated by thin layer chromatography (silica gel plates, 30% ethyl acetate in hexane). The volatile portion of the reaction mixture was removed by distillation under reduced pressure. The residue was purified by high pressure liquid chromatography (HPLC, 20% ethyl acetate in hexane, v/v). The purest fractions were combined. The solvent was removed under reduced pressure. The residue was crystallized to give 5.0 g of the title compound; mp 52°-54° C.; NMR (CDCl3) δ 1.45 (t, 3H), 1.7 (s, 6H), 3.02 (q, 2H), 9.0 (s, 1H); IR (CHCl3) 1720, 1700 cm-1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux until all the starting material
  3. customhad been consumed
  4. customThe volatile portion of the reaction mixture was removed by distillation under reduced pressure
  5. customThe residue was purified by high pressure liquid chromatography (HPLC, 20% ethyl acetate in hexane, v/v)
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was crystallized

Sources & evidence

ORD record
ord-e6587b2be0d14518b4018413b16f9be2
Source dataset
uspto-grants-1985_10
Patent number
US04547516

Reaction notes

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