3-(2H-pyran-4(3H,5H,6H)-ylidene)propan-1-ol → 3-(Oxan-4-yl)propan-1-ol

To a solution of 3-(2H-pyran-4(3H, 5H, 6H)-ylidene)propan-1-ol (13 g, 0.0916 mol) in methanol (260 mL) was added Pd(OH)2/C (1.3 g). The reaction flask was evacuated and filled with H2. Stirring was continued until the starting material had disappeared. The mixture was filtered through celite, and the filter cake was washed with MeOH (2×10 mL). The combined organic extracts were dried over Na2SO4, and concentrated under vacuum to give the product (11.8 g, 90%), which was used for the next step without purification. 1H NMR (CD3OD) δ 1.1-1.3 (m, 4H), 1.4-1.6 (m, 5H), 2.1-2.3 (s, 1H), 3.3-3.4 (t, 2H), 3.5-3.6 (t, 2H), 3.8-3.9 (dd, 2H).

1. customThe reaction flask was evacuated
2. additionfilled with H2
3. filtrationThe mixture was filtered through celite
4. washthe filter cake was washed with MeOH (2×10 mL)
5. dry with materialThe combined organic extracts were dried over Na2SO4
6. concentrationconcentrated under vacuum

ORD record

ord-c62cbf7aadc14e83b16bc6363ce7c985

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872028B2