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

HRID 2080113Notes

Reaction equation

HRID 2080113 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0d36fcdfba4d49b39c8d934b1b8c857c
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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