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

HRID 2080113노트

반응식

HRID 2080113 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0d36fcdfba4d49b39c8d934b1b8c857c
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

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