Methyl vinyl ketone → HCID 45085597, compound

Temperature

85 °C

To a solution of cyclopropanecarbaldehyde (3.20 ml, 42.8 mmol) in ethanol (15.3 mL) was added triethylamine (11.9 mL, 86.0 mmol), but-3-en-2-one (3.54 mL, 42.8 mmol), and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium bromide (2.16 g, 8.56 mmol). The reaction mixture was heated at 85° C. for 18.5 h. The reaction was then concentrated and the resulting residue was extracted with ethyl acetate (3×50 mL). The organic layer was dried (sodium sulfate), filtered and concentrated to an orange residue which was purified on silica gel on an automated system (ISCO 120 g, 20 mL/min) using 0 to 75% ethyl acetate in hexanes over 60 minutes. The product, 1-cyclopropylpentane-1,4-dione, was isolated as a yellow oil (2.21 g, 15.8 mmol, 37% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 2.86 (t, 2H), 2.72 (t, 2H), 2.19 (s, 3H), 1.90-1.99 (m, 1H), 1.01 (m, 2H), 0.88 (m, 2H).

1. concentrationThe reaction was then concentrated
2. extractionthe resulting residue was extracted with ethyl acetate (3×50 mL)
3. dry with materialThe organic layer was dried (sodium sulfate)
4. filtrationfiltered
5. concentrationconcentrated to an orange residue which
6. customwas purified on silica gel on an automated system (ISCO 120 g, 20 mL/min)
7. customover 60 minutes

ORD record

ord-8ce343f4b39245d78d6f2cf58177986e

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674115B2