Methyl vinyl ketone → 1-Cyclohexylpentane-1,4-dione
Reaction equation
[CH:1]1([CH:6]=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8](N(CC)CC)C.[CH3:15][C:16](=[O:19])[CH:17]=[CH2:18]>C(O)C.[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[CH:1]1([C:6](=[O:7])[CH2:18][CH2:17][C:16](=[O:19])[CH3:15])[CH2:8][CH2:2][CH2:3][CH2:4][CH2:5]1Participants
Conditions
- Temperature
- 85 °C
Procedure
To a solution of cyclopentanecarbaldehyde (2.00 g, 20.38 mmol) in ethanol (7.2 mL) was added triethylamine (5.68 mL, 40.8 mmol), but-3-en-2-one (1.69 mL, 26.7 mmol), and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium bromide (1.03 g, 4.08 mmol). The reaction mixture was heated at 85° C. for 72 hours after which it was concentrated. The resulting residue was extracted with ethyl acetate (3×50 mL) and the organic layers were dried (sodium sulfate), filtered and concentrated to an orange residue which was used in the next step without further purification. The crude product, 1-cyclohexylpentane-1,4-dione (3.68 g, 21.9 mmol) was isolated as an orange oil. 1H NMR (400 MHz, CDCl3) δ (ppm): 2.91 (m, 1H), 2.68-2.78 (m, 4H), 2.19 (s, 3H), 1.70-1.87 (m, 4H), 1.54-1.69 (m, 4H).
Workup
- concentrationwas concentrated
- extractionThe resulting residue was extracted with ethyl acetate (3×50 mL)
- dry with materialthe organic layers were dried (sodium sulfate)
- filtrationfiltered
- concentrationconcentrated to an orange residue which
- customwas used in the next step without further purification
Sources & evidence
- ORD record
- ord-528cb96024744393891cd283048112bd
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08674115B2
Reaction notes
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