Toluene → (Furo[2,3-b]pyridin-3-yl)methanol

Temperature

-75 °C

Diisobutylaluminium hydride in toluene (1.5M; 2.4 ml, 3.6 mmol) was added dropwise to a solution of methyl furo[2,3-b]pyridine-3-carboxylate (0.28 g, 1.58 mmol) in tetrahydrofuran (10 ml) at -75° C. The resulting solution was stirred at -75° C. for 40 minutes, the cooling bath removed and the mixture allowed to warm to room temperature. The reaction mixture was stirred at room temperature for 15 minutes, recooled to -40° C. and quenched by sequential addition of methanol (0.5 ml), water (0.25 ml) and 2M sodium hydroxide (0.25 ml). The mixture was allowed to warm up to produce a gel (exotherm observed), which was filtered off and washed with dichloromethane (8×10 ml). The filtrate was evaporated, the residue redissolved in dichloromethane and the solution dried (MgSO4). The solution was concentrated in vacuo to afford the title compound (0.2182 g, 93%) as a colourless solid; δH (CDCl3) 1.94 (1H, br s, CH2OH), 4.85 (2H, s, CH2OH), 7.26 (1H, dd, J 7.6, 4.9 Hz, 5-H), 7.69 (1H, s, 2-H), 8.05 (1H, dd, J 7.6, 1.7 Hz, 4-H), 8.34 (1H, dd, J 4.9, 1.7 Hz, 6-H).

1. customthe cooling bath removed
2. temperatureto warm to room temperature
3. stirringThe reaction mixture was stirred at room temperature for 15 minutes
4. customrecooled to -40° C.
5. customquenched by sequential addition of methanol (0.5 ml), water (0.25 ml) and 2M sodium hydroxide (0.25 ml)
6. temperatureto warm up
7. customto produce a gel (exotherm observed), which
8. filtrationwas filtered off
9. washwashed with dichloromethane (8×10 ml)
10. customThe filtrate was evaporated
11. dissolutionthe residue redissolved in dichloromethane
12. dry with materialthe solution dried (MgSO4)
13. concentrationThe solution was concentrated in vacuo

ORD record

ord-7dcf4a10bb0744e28a9f04cd8e576b2d

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05700802