3-(dihydro-2H-pyran-3(4H)-ylidene)propan-1-ol → 3-(Oxan-3-yl)propan-1-ol
Reaktionsgleichung
[O:1]1[CH2:6][CH2:5][CH2:4][C:3](=[CH:7][CH2:8][CH2:9][OH:10])[CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:2]1Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To the solution of compound 3-(dihydro-2H-pyran-3(4H)-ylidene)propan-1-ol (11.2 g, 0.0789 mol) in methanol (200 mL) was added Pd(OH)2/C (1.12 g). The reaction flask was degassed and filled into H2. Stirring was continued until the starting material disappeared. When the reaction was over, the mixture was filtered through celite, and the filter cake was washed with MeOH (2×10 mL). The combined organic layers were dried over Na2SO4, and concentrated in vacuo to give 3-(tetrahydro-2H-pyran-3-yl)propan-1-ol (10.35 g, yield 91%), which was used for the next step without purification. 1H NMR (CD3OD) δ 3.9-3.8 (m, 1H), 3.7-3.6 (m, 2H), 3.5-3.4 (m, 1H), 3.3 (m, 1H), 3.1-2.9 (t, 1H), 2.6-2.4 (m, 1H), 2.3-1.8 (m, 3H), 1.6-1.4 (m, 4H), 1.3-1.0 (m, 2H).