Hydrochloric Acid → (1E,6E)-1-(2-bromo-5-hydroxyphenyl)-7-(5-hydroxy-2-methoxyphenyl)hepta-1,6-diene-3,5-dione
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:9]=[CH:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14].B(OB=O)=O.[OH:22][C:23]1[CH:24]=[CH:25][C:26]([O:31][CH3:32])=[C:27]([CH:30]=1)[CH:28]=O.B(OCCCC)(OCCCC)OCCCC.C(N)CCC.Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11](=[O:16])[CH2:12][C:13](=[O:15])/[CH:14]=[CH:28]/[C:27]1[CH:30]=[C:23]([OH:22])[CH:24]=[CH:25][C:26]=1[O:31][CH3:32]Participants
Reactant 7
Product 1
Reagents, catalysts & solvents 2
Procedure
6-(2-Bromo-5-hydroxyphenyl)hex-5-ene-2,4-dione (15 mg, 53 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 mixture at 80° C. was added a solution of 5-hydroxy-2-methoxybenzaldehyde (10 mg, 0.07 mmol) and tri-n-butyl borate (25 mL, 93 μmol), sequentially. After the reaction mixture was 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 at room temperature, 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 (2.2 mg, 10%) as a solid.
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-1935f5ed3c1d4158b0dcf88e1eb9363d
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552220B2
Reaction notes
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