Hydrochloric Acid → HCID 68554935, compound
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=[O:15])[CH2:11][C:12](=[O:14])[CH3:13])=[CH:4][CH:3]=1.B(OB=O)=O.[OH:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[C:24]([O:30][CH3:31])[CH:23]=1.B(OCCCC)(OCCCC)OCCCC.C(N)CCC.Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C.[Cl-].[Na+].O>[OH:21][C:22]1[CH:29]=[CH:28][C:25](/[CH:26]=[CH:13]/[C:12](=[O:14])[CH2:11][C:10](=[O:15])[CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)=[C:24]([O:30][CH3:31])[CH:23]=1Participants
Reactant 7
Product 1
Reagents, catalysts & solvents 2
Procedure
6-(4-Hydroxyphenyl)hexane-2,4-dione (18 mg, 87 μmol) and boron trioxide (22 mg, 0.32 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. were added 4-hydroxy-2-methoxybenzaldehyde (12 mg, 78 μmol) and tri-n-butyl borate (50 μL, 0.19 mmol). After the reaction mixture was stirred for 2 h at the same temperature, n-butylamine (19 μL, 0.19 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 (11.6 mg, 44%) having the following characteristics.
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-40760a8e18ac4bbaab320bb57fd052cf
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962674B2
Reaction notes
Loading…