Butylamine → (1E,6E)-1-[4-diethylamino-2-(methoxymethoxy)phenyl]-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione

HRID 1854662Notes

Reaction equation

HRID 1854662 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]C.B(OB=O)=O.[CH2:23]([N:25]([CH2:38][CH3:39])[C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[C:28]([O:34][CH2:35][O:36][CH3:37])[CH:27]=1)[CH3:24].B(OCCCC)(OCCCC)O[CH2:42]CCC.C(N)CCC>C(OCC)(=O)C.[Cl-].[Na+].O>[CH2:23]([N:25]([CH2:38][CH3:39])[C:26]1[CH:33]=[CH:32][C:29](/[CH:30]=[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]([OH:8])=[C:2]([O:1][CH3:42])[CH:3]=2)=[C:28]([O:34][CH2:35][O:36][CH3:37])[CH:27]=1)[CH3:24]

Participants

8

Reactant 5

HCID 8007ButylamineHCID 12712Tributyl borateHCID 518682Boron trioxideHCID 143876754-Diethylamino-2-(methoxymethoxy)benzaldehydeHCID 570849216-(3-Hydroxy-4-methoxyphenyl)hex-5-ene-2,4-dione

Product 1

HCID 68552476(1E,6E)-1-[4-diethylamino-2-(methoxymethoxy)phenyl]-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dioneYield 149.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

6-(3-Hydroxy-4-methoxyphenyl)hex-5-ene-2,4-dione (20 mg, 0.085 mmol) and boron trioxide (11 mg, 0.16 mmol) were 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 4-diethylamino-2-(methoxymethoxy)benzaldehyde (26 mg, 0.11 mmol) and tri-n-butyl borate (25 μL, 93 μmol) in 0.7 mL of ethyl acetate. 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 resulting mixture was diluted with 25 mL of brine, and the solution was extracted with 50 mL of ethyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give a crude solid of (1E,6E)-1-[4-diethylamino-2-(methoxymethoxy)phenyl]-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione (57.8 mg).

Workup

  1. additionwas added
  2. extractionthe solution was extracted with 50 mL of ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1262e27b587f4618a669b06dda5fb1f2
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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