Tetrahydrofuran → HCID 86690128, Verbindung

A 1M solution of lithium tri-tert-butoxyaluminum hydride (8.79 mL, 8.79 mmol) was added dropwise to a cold (0° C.) stirred solution of diethyl tetrahydro-2H-pyran-2,2-dicarboxylate (0.810 g, 3.52 mmol) in an. THF (9 mL). After the addition is complete the mixture was allowed to warm to rt and heated to reflux for 4-5 h. The reaction mixture was cooled, diluted with ether and quenched with 20% NaHSO4 solution with vigorous stirring. The organic layer was separated, washed with brine and dried over MgSO4. The crude isolate was purified by silica gel FCC (5% MeOH in DCM) to afford ethyl 2-(hydroxymethyl)tetrahydro-2H-pyran-2-carboxylate as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.29 (q, J=7.0 Hz, 2H), 3.95-3.87 (m, 2H), 3.71 (dd, J=11.2, 8.2 Hz, 1H), 3.62 (dd, J=11.2, 5.1 Hz, 1H), 2.24-2.16 (m, J=8.0, 5.3 Hz, 1H), 2.14-2.06 (m, 1H), 1.84-1.72 (m, 1H), 1.64-1.50 (m, 4H), 1.37-1.29 (m, 3H).

1. additionAfter the addition
2. temperatureheated
3. temperatureto reflux for 4-5 h
4. temperatureThe reaction mixture was cooled
5. customquenched with 20% NaHSO4 solution with vigorous stirring
6. customThe organic layer was separated
7. washwashed with brine
8. dry with materialdried over MgSO4
9. customThe crude isolate
10. customwas purified by silica gel FCC (5% MeOH in DCM)

ORD-Eintrag

ord-63618eed7108464481f640c708e6de7a

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09326973B2