Butylamine → (1E,6E)-1,7-bis[4-(2-morpholinoethoxy)phenyl]hepta-1,6-diene-3,5-dione

HRID 632509

反応式

HRID 632509 の反応式
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[B]=O.[O:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][O:18][C:19]2[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=2)[CH2:12][CH2:11]1.[CH2:27](N)[CH2:28][CH2:29][CH3:30].[C:32]([O-:35])([O-])=O.[K+].[K+]>CCOC(C)=O.B(OCCCC)(OCCCC)OCCCC.C1COCC1>[O:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][O:18][C:19]2[CH:26]=[CH:25][C:22](/[CH:23]=[CH:1]/[C:2](=[O:7])[CH2:3][C:4](=[O:6])/[CH:5]=[CH:30]/[C:29]3[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH2:16][N:13]4[CH2:14][CH2:32][O:35][CH2:11][CH2:12]4)=[CH:27][CH:28]=3)=[CH:21][CH:20]=2)[CH2:12][CH2:11]1

参加物

9

反応物 5

HCID 8007ButylamineHCID 11430Potassium CarbonateHCID 31261AcetylacetoneHCID 37199024-(2-Morpholinoethoxy)benzaldehydeHCID 6327189Boron monoxide

生成物 1

HCID 117889043(1E,6E)-1,7-bis[4-(2-morpholinoethoxy)phenyl]hepta-1,6-diene-3,5-dione収率 24%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回HCID 12712Tributyl borate溶媒

反応条件

温度
70 °C

実験手順

To 2.0 g of pentane-2,4-dione were added 10.0 mL of AcOEt and 0.70 g of boron oxide, and the mixture was stirred at 70° C. for 1 hour. To the reaction mixture, 30 mL of a solution of 9.4 g of 4-(2-morpholinoethoxy)benzaldehyde in AcOEt and 10.7 mL of tributyl borate were successively added, and the mixture was stirred at the same temperature for 1 hour. To this, 0.4 mL of 1-butylamine was added, and the mixture was stirred at 70° C. for 2.5 hours and was allowed to cool back to room temperature. To the reaction mixture, 50 mL of a 10% K2CO3 aqueous solution and 30 mL of THF were added, and the mixture was stirred at room temperature for 10 minutes. The organic layer was separated, washed with saturated brine, dried over MgSO4, and concentrated. The residue was treated with 100 mL of diethyl ether to give 2.51 g of the title compound as a powder (24% yield).

後処理

  1. stirringthe mixture was stirred at the same temperature for 1 hour
  2. stirringthe mixture was stirred at 70° C. for 2.5 hours
  3. temperatureto cool back to room temperature
  4. stirringthe mixture was stirred at room temperature for 10 minutes
  5. customThe organic layer was separated
  6. washwashed with saturated brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. additionThe residue was treated with 100 mL of diethyl ether

出典と根拠

ORDレコード
ord-48d512c5912943118d34aa4458f6fa9f
出典データセット
uspto-grants-2016_04
特許番号
US09321752B2

関連ノート

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