Aniline → (2-(5-[1,3]Dioxolan-2-yl-furan-2-yl)-ethyl)-phenylamine

HRID 2080113ノート

反応式

HRID 2080113 の反応式
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[O:10][C:9]([CH2:11][CH:12]=O)=[CH:8][CH:7]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O1CCCC1.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[O:10][C:9]([CH2:11][CH2:12][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:7]=1

参加物

6

反応物 4

HCID 6115AnilineHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 86042298(5-[1,3]Dioxolan-2-yl-furan-2-yl)-acetaldehyde

生成物 1

HCID 23130754(2-(5-[1,3]Dioxolan-2-yl-furan-2-yl)-ethyl)-phenylamine収率 20.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Next, the resulting (5-[1,3]dioxolan-2-yl-furan-2-yl)-acetaldehyde (1.57 g), aniline (0.94 mL, 10.3 mmol) and triacetoxy sodium borohydride (3.76 g, 17.2 mmol) were suspended in a mixture solution of tetrahydrofuran (30 mL) and acetic acid (1 mL) at 0° C., and the mixture was stirred at room temperature for 19 hours. An aqueous solution of saturated sodium bicarbonate was added to the reaction mixture at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1), and the title compound (453 mg, 1.75 mmol, 14%) was obtained as a brown oil.

後処理

  1. extractionwhich was then extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-0d36fcdfba4d49b39c8d934b1b8c857c
出典データセット
uspto-grants-2011_04
特許番号
US07932272B2

反応ノート

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