3,4-dihydro-2H-pyran → 1-Pentanol, 5-[(tetrahydro-2H-pyran-2-yl)oxy]-

Temperature

0 °C

To a mixture of pentane-1,5-diol(5.2 g, 0.05 mol) and p-toluenesulfonic acid (0.1g, 0.53 mmol) in CH2Cl2 (120 mL) was added slowly dihydro-2H-pyran (4.6 g, 0.055 mol) in CH2Cl2 (30 mL) at 0° C. After stirring for 2 h at 0° C. and for another 1 h at room temperature, saturated NaHCO3 (50 mL ) was added to the reaction mixture. The CH2Cl2 layer was washed with saturated NaHCO3 (50 mL), water (50 mL), and dried (MgSO4). The residue was purified by column chromatography on silica gel with EtOAc:hexane (1:1, v/v) and subsequent Kugelrohr distillation to give the title product (4, 5.1 g, 54%); bp 80°-85° C./0.1 torr; IR(neat): 3450 (broad) and 1135 cm-1 ; 1H NMR: 1.3-1.9 (m, 12H), 2.4 (b s, 1H ), 3.3-3.9 ( m, 6H ), and 4.58 ppm (m, 1H ).

1. washThe CH2Cl2 layer was washed with saturated NaHCO3 (50 mL), water (50 mL)
2. dry with materialdried (MgSO4)
3. customThe residue was purified by column chromatography on silica gel with EtOAc:hexane (1:1
4. distillationv/v) and subsequent Kugelrohr distillation

ORD record

ord-3d70c8a5a32645fc9f47bff1284e6302

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05571689