Dimethylformamide → HCID 53718720, compound

Methyl 2-(1-carboxy-1-chloromethylene)-1,3-dithietane-4-carboxylate (1.29 g) and oxalyl chloride (700 μl) are reacted together in ethyl ether in the presence of N,N-dimethylformamide (50 μl), and the reaction mixture is concentrated under reduced pressure. The resulting residue comprising methyl 2-(1-chlorocarbonyl-1-chloromethylene)-1,3-dithietane-4-carboxylate is dissolved in THF (70 ml) and reacted with lithium tri-t-butoxyalminum hydride (1.36 g) at -78° C. for 30 minutes. The reaction mixture is diluted with a mixture of ethyl acetate and dil. HCl, and the organic layer is separated after vigorous stirring. The separated organic layer is dried, vacuum concentrated, and purified by chromatography over silica gel to give methyl 2-(1-chloro-1-formylmethylene)-1,3-dithietane-4-carboxylate. Yield: 328 mg (27%).

1. concentrationthe reaction mixture is concentrated under reduced pressure
2. dissolutionThe resulting residue comprising methyl 2-(1-chlorocarbonyl-1-chloromethylene)-1,3-dithietane-4-carboxylate is dissolved in THF (70 ml)
3. customreacted with lithium tri-t-butoxyalminum hydride (1.36 g) at -78° C. for 30 minutes
4. customthe organic layer is separated after vigorous stirring
5. customThe separated organic layer is dried
6. concentrationvacuum concentrated
7. custompurified by chromatography over silica gel

ORD record

ord-6b963b2990104a289eee76d8c27f3699

Source dataset

uspto-grants-1985_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04529721