Tetrahydrofuran → HCID 18007583, compound

Temperature

0 °C

To a 250 mL round bottom flask equipped with a stir bar was added compound (i), above, (3.0 g; 10.6 mmol) and THF (50 mL). The mixture was cooled to 0° C. and diisobutylaluminium hydride (1M in toluene)(42.5 mL; 42.5 mmol) added. The reaction mixture was stirred at room temperature for 2 h, cooled to 0° C. and the quenched with sodium sulfate decahydrate. The resulting thick gel was refluxed for 1 h, after which it was filtered through a pad of celite. Upon removing the solvent in vacuo a yellow oil was isolated, which was subjected to column chromatography on silica gel using hexanes:ethyl acetate (90:10) to yield the title compound as a bright greenish-yellow oil (1.8 g; 71%). 13C NMR (CDCl3): δ 136.9, 129.1, 127.5, 122.8,122.3, 115.3, 122.5, 101.8, 61.7, and 48.7.

1. customTo a 250 mL round bottom flask equipped with a stir bar
2. temperaturecooled to 0° C.
3. customthe quenched with sodium sulfate decahydrate
4. temperatureThe resulting thick gel was refluxed for 1 h
5. filtrationafter which it was filtered through a pad of celite
6. customUpon removing the solvent in vacuo a yellow oil
7. customwas isolated

ORD record

ord-527c53ab21f741abba8b0f993f42e6ac

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06380242B1