Hydrochloric Acid → HCID 10019238, compound
Reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[S:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>O1CCCC1>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[S:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 0.241 g (0.59 mmol) ethyl 8-(2-tetrahydropyranyloxy)-4-[3-(3-pyridyl)propyl]-3thia-octanoate in 1 ml tetrahydrofuran is added 1 mL of 1N hydrochloric acid. After stirring for 1 hour at room temperature, thin layer chromatography indicates incomplete conversion. Another 0.35 mL of 6N hydrochloric acid is added and the mixture is stirred for 1 hour. The pH of the reaction mixture is then adjusted to 8.0 and the resulting solution is extracted with methylene chloride. The organic layer is washed with brine, dried, filtered and evaporated to give yellow oil which is purified by preparative thin layer chromatography over silica gel using ether/ethyl acetate (4:1) as eluent to give ethyl 8-hydroxy-4-[3-(3-pyridyl)propyl]-3-thia-octanoate; IR (CH2Cl2) 3679, 1730 cm-1.