Thionyl Chloride → HCID 18367388, compound

Participants

Reaction Steps

To a solution of 1-[[4-hydroxy-1-(4,5-diphenyloxazol-2-yl)butyl]amino]-5-methoxy-1,2,3,4-tetrahydronaphthalene (0.9 g) in CH2Cl2 (20 ml) was added SOCl2 (3 ml). After being stirred for 4 hours, the solvent was removed. The residue was dissolved in CH3CN (20 ml) and K2CO3 (5 g) was added to the solution. After being stirred for 4 hours under reflux, the solution was poured into the mixture of ethyl acetate and water. The organic layer was washed with water and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-[2-(4,5-diphenyloxazol-2-yl)pyrrolidin-1-yl]-5-methoxy-1,2,3,4-tetrahydronaphthalene (0.57 g). MS (m/z): 451 (M+ +1) IR (Neat): 1580 cm-1NMR (CDCl3, δ): 1.5-2.3 (8H, m), 2.4-3.2 (4H, m), 3.69 and 3.76 (3H, each s), 4.0-4.2 (2H, m), 6.4-6.72 (3H, m), 7.3-7.7 (10H, m)

Provenance & Evidence