Methyl vinyl ketone → 1-Cyclohexylpentane-1,4-dione

Temperature

85 °C

To a solution of cyclohexanecarbaldehyde (3.22 mL, 26.7 mmol) in ethanol (9.5 mL) was added triethylamine (7.46 mL, 53.5 mmol), but-3-en-2-one (2.22 mL, 26.7 mmol), and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium bromide (1.35 g, 5.35 mmol). The reaction mixture was heated at 85° C. for 18.5 hours. The reaction was then concentrated under vacuum 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 using an automated system (ISCO 120 g, 20 mL/min) and 0 to 45% ethyl acetate in hexanes over 60 minutes as the eluent. The product was isolated as a yellow oil (1.32 g, 7.24 mmol, 27% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 2.68-2.73 (m, 4H), 2.35-2.42 (m, 1H), 2.19 (s, 3H), 1.85-1.89 (m, 2H), 1.76-1.79 (m, 2H), 1.65-1.69 (m, 1H), 1.17-1.39 (m, 5H).

1. concentrationThe reaction was then concentrated under vacuum
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 using an automated system (ISCO 120 g, 20 mL/min) and 0 to 45% ethyl acetate in hexanes over 60 minutes as the eluent

ORD record

ord-1a2638d5b4d74890985acdc8e5c676e5

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674115B2