反应详情

A solution of 2-hydroxymethyl-1,2,3,4-tetrahydronaphthalene (2.28 g, 14.0 mmol) in 100 ml of CH2Cl2 was treated with PBr3 (1.28 g, 4.73 mmol) at 0° C. The mixture was stirred at room temperature for 72 hours then poured onto 100 g of ice. The organic layer was isolated, washed with 10% K2CO4 aqueous solution, H2O, sat'd brine, and then dried over Na2SO4. After filtration and removal of solvent, the residue was purified by chromatography (SiO2, F. tOAc:hexane, 1:10) to give a colorless oil (1.33 g, 41.6%); 1H NMR (CDCl3, 300 g MHz)δ 1.55 (m, 1H) , 2.11 (m, 1H) , 2.11 (m, 2H) , 2.58 (dd, J1 =16.2 Hz, J2 =10.2 Hz, 1H) , 2.80-3.10 (m, 3H) , 3.45 (d, J=6.3 Hz, 2H), 7.10 (m, 4H).

1. customThe organic layer was isolated
2. washwashed with 10% K2CO4 aqueous solution, H2O
3. dry with materialdried over Na2SO4
4. filtrationAfter filtration and removal of solvent
5. customthe residue was purified by chromatography (SiO2, F. tOAc:hexane, 1:10)