Ethyl tetrahydropyran-4-ylacetate → 2-(Oxan-4-yl)ethan-1-ol

Temperature

0 °C

To a suspension of lithium aluminium hydride (11 g, 0.29 mol) in dry tetrahydrofuran (350 mL) at 0° C. was added a solution of (tetrahydro-pyran-4-yl)-acetic acid ethyl ester (25 g, 0.145 mol) in dry tetrahydrofuran (100 mL) dropwise. The resulting mixture was then refluxed for 16 h. After cooling to 0° C., the reaction mixture was quenched carefully by slow addition of a saturated sodium carbonate solution (50 mL). The mixture was decanted and the precipitate was washed with tetrahydrofuran (2×200 mL). The combined tetrahydrofuran layers were dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-(tetrahydro-pyran-4-yl)-ethanol (13 g, 69%) as a yellow oil which was used in the next step without purification.

1. temperatureThe resulting mixture was then refluxed for 16 h
2. customthe reaction mixture was quenched carefully by slow addition of a saturated sodium carbonate solution (50 mL)
3. customThe mixture was decanted
4. washthe precipitate was washed with tetrahydrofuran (2×200 mL)
5. dry with materialThe combined tetrahydrofuran layers were dried over anhydrous sodium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-ff0fab5b78bd4b2ca46c03257749bce0

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222416B2