Thionyl Chloride → cis-2-Pentenyl 5-aminolevulinate hydrochloride
Reaction equation
S(Cl)([Cl:3])=O.Cl.[NH2:6][CH2:7][C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12]>CN(C)C=O>[ClH:3].[NH2:6][CH2:7][C:8](=[O:14])[CH2:9][CH2:10][C:11]([O:13][CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH3:11])=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 1 ml of thionyl chloride (SOCl2) were added 3 drops of N,N-dimethylformamide (DMF) with stirring. Following the addition of 5-aminolevulinic acid hydrochloride (ALA.HCl, 200 mg, 1.19 mol), the solution was stirred for 12 hours at room temperature. Concentration in a vacuum was conducted before the addition of cis-2-pentenol. Then, the reaction mixture was stirred for 1.5 hours at room temperature, followed by purification by silica gel chromatography to afford cis-2-pentenyl 5-aminolevulinate hydrochloride at a yield of 68%.