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

HRID 1854661노트

반응식

HRID 1854661 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매2회HCID 57417360Sodium chloride; water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3f77e5207c724258b2d19af14a890e77
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962674B2

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