Hydrochloric Acid → (1E,6E)-1-(3-fluoro-4-hydroxyphenyl)-7-(3-hydroxy-4-methoxyphenyl)hepta-1,6-diene-3,5-dione
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12](=[O:17])[CH2:13][C:14](=[O:16])[CH3:15])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].B(OB=O)=O.[F:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[OH:32])[CH:27]=O.B(OCCCC)(OCCCC)OCCCC.C(N)CCC.Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.[Cl-].[Na+].O>[F:23][C:24]1[CH:25]=[C:26](/[CH:27]=[CH:15]/[C:14](=[O:16])[CH2:13][C:12](=[O:17])/[CH:11]=[CH:10]/[C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([OH:1])[CH:3]=2)[CH:29]=[CH:30][C:31]=1[OH:32]Participants
Reactant 7
Product 1
Reagents, catalysts & solvents 2
Procedure
6-(3-Hydroxy-4-methoxyphenyl)hex-5-ene-2,4-dione (20 mg, 85 μmol) and boron trioxide (11 mg, 0.16 mmol) was placed in a 20 mL reaction vessel, and dissolved in 0.4 mL of ethyl acetate. To the stirring solution at 80° C. was added a solution of 3-fluoro-4-hydroxybenzaldehyde (15 mg, 0.11 mmol) and tri-n-butyl borate (25 μL, 93 μmol) in 0.7 mL of ethyl acetate. After being stirred for 2 h at the same temperature, n-butylamine (10 μL, 0.10 mmol) was added with additional stirring for 1 h. The reaction mixture was treated with a 1:1 solution (1 mL) of 1N HCl and brine, and was stirred at 50° C. for 5 min to 1 h (if necessary, the reaction mixture was neutralized by saturated NaHCO3 aqueous solution). The organic layer was purified directly by silica gel column chromatography (eluting with hexane/ethyl acetate or chloroform/methanol) to obtain the title compound as a solid (14.4 mg, 47%).
Workup
- additionwas added
- stirringwas stirred at 50° C. for 5 min to 1 h (if necessary, the reaction mixture
- customThe organic layer was purified directly by silica gel column chromatography (eluting with hexane/ethyl acetate or chloroform/methanol)
Sources & evidence
- ORD record
- ord-fe7f81aeb8f748698e22b2b31b329e29
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962674B2
Reaction notes
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