Reaction #2358494

Reaction equation

Tert-butyl (3E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylene]-2-oxo-azepane-1-carboxylate

hydrogen chloride

→

(3E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylene]azepan-2-one

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Washthe reaction mixture was washed with sat. NaHCO3
2. 2
   ExtractionThe aqueous layer was extracted once with dichloromethane
3. 3
   Dryingdried over Na2SO4
4. 4
   Otherthe solvent was evaporated
5. 5
   Otherto give the crude as a yellow solid
6. 6
   OtherThe residue was triturated in tertbutylmethylether
7. 7
   Filtrationthe solid was filtered
8. 8
   Otherdried

Procedure

Tert-butyl (3E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylene]-2-oxo-azepane-1-carboxylate I-13b (0.55 g) was solved in dichloromethane (20 mL) and hydrogen chloride (2.0378 mL, 4M in dioxane) was added dropwise. After 30 min., dichloromethane was added and the reaction mixture was washed with sat. NaHCO3. The aqueous layer was extracted once with dichloromethane, the organic layers were combined, dried over Na2SO4 and the solvent was evaporated to give the crude as a yellow solid. The residue was triturated in tertbutylmethylether and the solid was filtered and dried to give (3E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylene]azepan-2-one Ia-13 (0.245 g, 63%) as a white solid. LCMS (Method D): 0.67 min; ES+238 (M+H+).

Source