Thionyl Chloride → HCID 58598870, compound
Reaction equation
S(Cl)(Cl)=[O:2].[C:5]1(=[N:16]O)[CH:8]2[CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[CH:7]2[CH2:6]1>O1CCOCC1>[C:5]1(=[O:2])[CH:8]2[CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[CH:7]2[CH2:6][NH:16]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Thionyl chloride (1.9 mL, 26.4 mmol) was added to a solution of 2,2a,7,7a-tetrahydro-cyclobuta[a]inden-1-one oxime (1.5 g, 8.8 mmol) in 1,4-dioxane (44 mL), and stirred overnight at room temperature. The reaction was quenched with saturated aqueous NaHCO3 (100 mL), and extracted with EtOAc (3×50 mL). The organic extracts were washed with brine, dried over MgSO4, and concentrated to give the subtitle compound and its regioisomer, which were used without further purification. MS calculated for C11H11NO+H: 174, observed: 174.