Hydrochloric Acid → HCID 68550659, compound
Reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].B(OB=O)=O.[O:13]1[C:18]2[CH:19]=[CH:20][C:21]([CH:23]=O)=[CH:22][C:17]=2[O:16][CH2:15][CH2:14]1.B([O:36][CH2:37][CH2:38][CH2:39][CH3:40])(OCCCC)OCCCC.[CH2:41](N)CCC.Cl.C([O-])(O)=O.[Na+].[C:52]([O:55][CH2:56][CH3:57])(=O)[CH3:53]>[Cl-].[Na+].O>[O:36]1[C:37]2[CH:38]=[CH:39][C:40](/[CH:41]=[CH:6]/[C:5](=[O:7])[CH2:4][C:1](=[O:3])/[CH:2]=[CH:23]/[C:21]3[CH:20]=[CH:19][C:18]4[O:13][CH2:14][CH2:15][O:16][C:17]=4[CH:22]=3)=[CH:57][C:56]=2[O:55][CH2:52][CH2:53]1Participants
Reactant 8
Product 1
Reagents, catalysts & solvents 1
Procedure
Acetylacetone (10.3 μL, 100 μmol) and boron trioxide (25 mg, 0.40 mmol) was placed in a 20 mL reaction vessel, and dissolved in 0.45 mL of ethyl acetate. To the stirring solution at 80° C. were added 1,4-benzodioxane-6-carboxaldehyde (41 mg, 0.25 mmol) and tri-n-butyl borate (57 μL, 0.21 mmol), successively. After the reaction mixture was stirred for 2 h at the same temperature, n-butylamine (22 μL, 0.22 mmol) was added with additional stirring for 1 h. The reaction mixture was treated with a 1:1 solution (3 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 with 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 (20.0 mg, 51%) 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-63359ee06dc04966a7acac07e14c1dbd
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962674B2
Reaction notes
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