Ethanone, 1-(2,6,6-trimethyl-3-cyclohexen-1-yl)- → 4-(2,6,6-Trimethyl-cyclohex-3-enyl)-pyrimidine
Reaction equation
[CH3:1][CH:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH:3]1[C:10](=O)[CH3:11].[C:13](O)(=O)C.[CH:17]([NH2:19])=[NH:18]>C(O)CCC>[CH3:1][CH:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH:3]1[C:10]1[CH:11]=[CH:13][N:19]=[CH:17][N:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A 100 mL reaction flask is charged with 1-(2,6,6-trimethyl-cyclohex-3-enyl)-ethanone (10 g, 0.06 mol, commercially available at IFF), formamidine acetate (31 g, 0.3 mol), and butanol (50 mL). The reaction mixture is heated to 130° C. and stirred for 24 hours. The crude mass is washed once with aqueous sulfuric acid (10%, 100 mL) followed by twice with brine (30 mL). Butanol is recovered by roto-evaporation. The crude product is further purified with liquid chromatography (Biotage® system) and then crystallized. Product 4-(2,6,6-trimethyl-cyclohex-3-enyl)-pyrimidine (˜10 g) is obtained.
Workup
- customA 100 mL reaction flask
- washThe crude mass is washed once with aqueous sulfuric acid (10%, 100 mL)
- customButanol is recovered by roto-evaporation
- customThe crude product is further purified with liquid chromatography (Biotage® system)
- customcrystallized
Sources & evidence
- ORD record
- ord-a1727489154b4c70a8df947aa6efc84a
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557876B2
Reaction notes
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