Ethanethiol → 5-[Bis(ethylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
Reaction equation
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]Participants
Procedure
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).
Workup
- extractionThe resultant mixture was extracted with ethyl acetate
- washThe combined extracts were washed with water
- dry with materialdried (MgSO4)
- concentrationconcentrated to dryness under reduced pressure
- customThe residue was purified by HPLC (20% ethyl acetate in hexane, v/v)
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-1e286971a61643f58f9db9924f333c58
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04547516
Reaction notes
Loading…