2-Thienyl ketone → Dithiophen-2-ylmethanol

Temperature

-40 °C

To a -35° to -40° C. solution of 2-(then-2-oyl)thiophene (Maybridge of Cornwall, UK) (500 mg, 2.60 mmol) in 10 mL of methylene chloride, is added dropwise a 1M solution of diisobutylaluminum hydride in methylene chloride (6.50 mL, 6.50 mmol) over 20 minutes. The reaction is stirred at -40° C. for 2.5 hours and then quenched by the slow addition of 10 mL of methanol. The mixture is warmed to room temperature and poured into 100 mL of saturated aqueous sodium tartrate. The aqueous solution is extracted with several portions of methylene chloride, the organic extracts combined, and dried over magnesium sulfate. Chromatography on silica gel, eluting with a 1:2 mixture of ethyl acetate to hexane, gives di-2-thienylmethanol as a light orange solid in 54% yield.

1. customquenched by the slow addition of 10 mL of methanol
2. temperatureThe mixture is warmed to room temperature
3. additionpoured into 100 mL of saturated aqueous sodium tartrate
4. extractionThe aqueous solution is extracted with several portions of methylene chloride
5. dry with materialdried over magnesium sulfate
6. washChromatography on silica gel, eluting with a 1:2 mixture of ethyl acetate to hexane

ORD record

ord-0064425b136948878c7e30a52df949ec

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05571825