3-(dihydro-2H-pyran-3(4H)-ylidene)propan-1-ol → 3-(Oxan-3-yl)propan-1-ol

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 with H2. 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 further 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).

1. customThe reaction flask was degassed
2. additionfilled with H2
3. filtrationwas filtered through celite
4. washthe filter cake was washed with MeOH (2×10 mL)
5. dry with materialThe combined organic layers were dried over Na2SO4
6. concentrationconcentrated in vacuo

ORD record

ord-e585954443a242eba27331643b4b8a89

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08487108B2