Diethyl Ether → (6-(Propan-2-yl)pyridin-2-yl)methanol

Temperature

0 °C

Ethyl 6-isopropylpicolinate (prepared as in Preparation C; 75 g, 0.39 mol) was dissolved in 1.5 liters of dry THF, chilled to 0° C. and lithium aluminum hydride (0.39 L, 0.39 mol, 1M in THF) was added slowly over a 20 minute period. The resulting dark solution was stirred at 0° C. for 30 minutes, then allowed to warm to ambient temperature. TLC showed complete consumption of starting material. The reaction mixture was chilled to 0° C. and quenched carefully by the addition of sodium sulfate decahydrate until no gas evolution was observed. A thick mixture resulted. Celite and ether (about 200 mL) were added and the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to give 32 g of brown oil. The filter cake was slurried in IPA/EtOAc overnight and filtered to give an additional 8 g of product (68%).

1. temperatureto warm to ambient temperature
2. customconsumption of starting material
3. temperatureThe reaction mixture was chilled to 0° C.
4. customquenched carefully by the addition of sodium sulfate decahydrate until no gas evolution
5. customA thick mixture resulted
6. filtrationthe reaction mixture was filtered
7. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-e3d4198cf1494d29870de86001db7457

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174981B2