Triethylamine → HCID 53865625, compound

Temperature

1 °C

In an oven-dried three-necked flask were placed a mixture of 3-(furan-3-yl)prop-2-enoic acid (20.0 g, 145 mmol) and dry triethylamine (17.2 g, 171 mmol) in acetone (200 mL, dried over anhydrous MgSO4). The mixture was cooled to 0 to 2° C. To the cold mixture, isobutyl chloroformate (25.2 mL, 193 mmol) was added at 0° C. The mixture was stirred at 0 to 2° C. for 30 min, then a solution of sodium azide (14.0 g, 215 mmol) in water (60 mL) was added slowly at 0° C. The reaction mixture was stirred for 1 h at the same temperature. It was quenched with an ice-water (500 mL) and the title azide was extracted with toluene (4×100 mL), dried over an anhydrous sodium sulfate and filtered. The filtrate containing the crude title compound was used as such for the next reaction.

1. customIn an oven-dried three-necked flask were placed
2. stirringThe reaction mixture was stirred for 1 h at the same temperature
3. customIt was quenched with an ice-water (500 mL)
4. extractionthe title azide was extracted with toluene (4×100 mL)
5. dry with materialdried over an anhydrous sodium sulfate
6. filtrationfiltered
7. additionThe filtrate containing the crude title compound
8. customsuch for the next reaction

ORD record

ord-e81c1164ab334cc9bd99df0dcd6ec070

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08378104B2