Hydrochloric Acid → HCID 21467676, compound

Temperature

-78 °C

To a suspension of 7.02 g (68.7 mmol) of N,N'-trimethylethylene diamine in 100 ml of anhydrous tetrahydrofuran (chilled to -78° C.) was added 44.6 ml (71.4 mmol) of 1.6M n-BuLi in hexanes. A dark yellow solution was formed. The solution was stirred at -78° C. under a blanket of argon for 15 minutes. To the solution was added 6.24 g (64.9 mmol) of distilled 3-furaldehyde and the solution was stirred at -78° C. for 20 minutes. To this solution was added 55.0 ml (71.4 mmol) of 1.3M solution of BuLi in hexanes and the solution was stirred at -78° C. for 3 hours. The anion formed was transfered via cannula onto a solution of 7.75 g (6.8 ml, 71.4 mmol) of ethyl chloroformate in 20 ml of anhydrous tetrahydrofuran (chilled to -78° C.). The resulting solution was allowed to warm to room temperature and stirred overnight (16.33 h). The solution was poured onto 1:10 10% HCl: ice (v/v) and the layers were separated. The aqueous layer was extracted with ether and the organic phases combined, dried over MgSO4, filtered and concentrated in vacuo to yield a brown oil. Purification by flash chromatography (silica gel, 5% ethyl acetate in hexane) yielded the title compound as a white solid.

1. customA dark yellow solution was formed
2. stirringthe solution was stirred at -78° C. for 20 minutes
3. stirringthe solution was stirred at -78° C. for 3 hours
4. customThe anion formed
5. temperatureto warm to room temperature
6. stirringstirred overnight (16.33 h)
7. customice (v/v) and the layers were separated
8. extractionThe aqueous layer was extracted with ether
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customto yield a brown oil
13. customPurification by flash chromatography (silica gel, 5% ethyl acetate in hexane)

ORD record

ord-753ba52be3054557b2c9b6163ca29063

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05696162