Toluene → Benzofuran-3-ylmethanol

Temperature

-75 °C

Diisobutylaluminium hydride in toluene (1.5M, 16.8 ml, 25.2 mmol) was added dropwise to a solution of methyl benzo[b]furan-3-carboxylate (2.02 g, 11.5 mmol) in tetrahydrofuran (50 ml) at -75° C. The resulting solution was stirred at -75° C. for 30 minutes, the cooling bath removed and the mixture allowed to warm to room temperature. The reaction mixture was recooled to -40° C. and quenched by sequential addition of methanol (3 ml), water (1.5 ml) and 2M sodium hydroxide (1.5 ml). The mixture was allowed to warm up to produce a gel, which was filtered off and washed with dichloromethane (6×50 ml). The filtrate was evaporated to dryness, the residue redissolved in ether and the solution dried over magnesium sulphate. The solution was evaporated to afford the title compound (1.66 g, 98%) as an oil which crystallised on standing; δH (CDCl3) 1.61 (1H, br s, OH), 4.85 (2H, s, C H2OH), 7.25-7.35 (2H, m, ArH), 7.49 (1H, dd, J 7.8, 1.0 Hz, ArH), 7.61 (1H, s, 2-H), 7.67 (1H, m, ArH).

1. customthe cooling bath removed
2. temperatureto warm to room temperature
3. customwas recooled to -40° C.
4. customquenched by sequential addition of methanol (3 ml), water (1.5 ml) and 2M sodium hydroxide (1.5 ml)
5. temperatureto warm up
6. customto produce a gel, which
7. filtrationwas filtered off
8. washwashed with dichloromethane (6×50 ml)
9. customThe filtrate was evaporated to dryness
10. dissolutionthe residue redissolved in ether
11. dry with materialthe solution dried over magnesium sulphate
12. customThe solution was evaporated

ORD record

ord-b536ffb5cad143e499d6e0ee54b5f05a

Source dataset

uspto-grants-1997_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05665722