Triethylamine → 3-Diazopentane-2,4-dione

Temperature

0 °C

A 1-L round-bottomed flask was charged with acetylacetone (S1) (10.25 mL, 100 mmol, 1.0 equiv) and acetonitrile (600 mL). p-Acetamidobenzene sulfonyl azide (p-ABSA)(J. S. Baum et al., Synth. Commun. 17, 1709 (1987) (24.0 g, 100 mmol, 1.0 equiv) was added and the reaction was cooled to 0° C. Triethylamine (NEt3) (41.8 mL, 300 mmol, 3 equiv) was added dropwise and the reaction was warmed to rt for 1 hour. The resulting suspension was filtered through a fitted funnel and concentrated. The obtained residue was triturated with 1:1 ether:petroleum ether and the precipitated white solids were removed via filtration. Solvents were removed in vacuo providing analytically pure S2 as a yellow oil in quantitative yield. Spectral data matched those reported in the literature (Z.-B. Chem et al., J. Org. Chem. 74, 903 (2009)).

1. addition17, 1709 (1987) (24.0 g, 100 mmol, 1.0 equiv) was added
2. temperaturethe reaction was warmed to rt for 1 hour
3. filtrationThe resulting suspension was filtered through a fitted funnel
4. concentrationconcentrated
5. customThe obtained residue was triturated with 1:1 ether
6. custompetroleum ether and the precipitated white solids were removed via filtration
7. customSolvents were removed in vacuo
8. customproviding analytically pure S2 as a yellow oil in quantitative yield

ORD record

ord-ee3fa867a1a54c058a5deb283770c682

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09399652B2