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

HRID 1854661ノート

反応式

HRID 1854661 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:15])[CH2:11][C:12](=[O:14])[CH3:13])=[CH:4][C:3]=1[O:16][CH3:17].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)OCCCC.C(N)CCC>C(OCC)(=O)C.[Cl-].[Na+].O>[CH2:38]([N:25]([CH2:23][CH3:24])[C:26]1[CH:33]=[CH:32][C:29](/[CH:30]=[CH:13]/[C:12](=[O:14])[CH2:11][C:10](=[O:15])/[CH:9]=[CH:8]/[C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:16][CH3:17])[CH:4]=2)=[C:28]([O:34][CH2:35][O:36][CH3:37])[CH:27]=1)[CH3:39]

参加物

8

反応物 5

HCID 8007ButylamineHCID 12712Tributyl borateHCID 518682Boron trioxideHCID 143876754-Diethylamino-2-(methoxymethoxy)benzaldehydeHCID 543188196-(4-Hydroxy-3-methoxyphenyl)hex-5-ene-2,4-dione

生成物 1

HCID 68552476(1E,6E)-1-[4-diethylamino-2-(methoxymethoxy)phenyl]-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione収率 159.5%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

6-(4-Hydroxy-3-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 extract 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 (61.5 mg).

後処理

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

出典と根拠

ORDレコード
ord-3f77e5207c724258b2d19af14a890e77
出典データセット
uspto-grants-2015_02
特許番号
US08962674B2

反応ノート

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