Furan → HCID 12374798, compound

Furan was added dropwise to a stirred solution of n-butyllithium (2.5M in hexanes, 58.8 ml, 147 mmol) in dry THF (200 ml) at -20° C. under argon. The mixture was allowed to warm to room temperature and was then heated at reflux for 4 h. The mixture was cooled to -30° C. and isovaleraldehyde (12.8 g, 147 mmol) was added dropwise. The mixture was allowed to warm to room temperature and was then heated at reflux for 16 h. The reaction mixture was allowed to cool to room temperature, poured onto crushed ice, extracted with ether and the combined organic extracts dried over anhydrous potassium carbonate, filtered and concentrated to give a dark yellow oil. Distillation under reduced pressure gave 1-(2-furyl)-3-methylbutanol (11.0 g, 49%) as a colourless oil.

1. temperaturewas then heated
2. temperatureat reflux for 4 h
3. temperatureThe mixture was cooled to -30° C.
4. temperatureto warm to room temperature
5. temperaturewas then heated
6. temperatureat reflux for 16 h
7. temperatureto cool to room temperature
8. additionpoured
9. customonto crushed ice
10. extractionextracted with ether
11. dry with materialthe combined organic extracts dried over anhydrous potassium carbonate
12. filtrationfiltered
13. concentrationconcentrated
14. customto give a dark yellow oil
15. distillationDistillation under reduced pressure

ORD record

ord-0c76ebf7b3e0415fbb7b31a071143f7e

Source dataset

uspto-grants-1996_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05516783