3,4-dihydro-2H-pyran → 2-Hydroxy-5-(tetrahydro-pyran-2-yloxy)-benzaldehyde

반응식

[OH:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][O:11]2)=[CH:6][C:3]=1[CH:4]=[O:5]

참가 물질

실험 절차

A solution of 2,5-dihydroxy-benzaldehyde (152 mmol), 3,4-dihydro-2H-pyran (167 mmol) and a catalytic amount of pyridinium p-toluenesulfonate in CH2Cl2 (480 mL) was left overnight at room temperature. The organic phase was washed with 1 N Na7CO3 (aq) (3×100 mL) and dried (Na2SO4). Evaporation in vacuo gave the desired product as brown crystals that was used without further purification. 1H-NMR (CDCl3) δ 10.72 (s, 1H), 9.88 (s, 1H), 7.32-7.29 (m, 2H), 6.96 (d, 1H), 5.38 (bs, 1H), 3.99-3.91 (m, 1H), 3.69-3.64 (m, 1H), 2.06-1.63 (m, 6H).