Acetic Acid → HCID 18938795, compound

HRID 356667Notes

Reaction equation

HRID 356667 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:8]1[CH:12]=[CH:11][C:10]([CH:13]=O)=[CH:9]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[O:8]1[CH:12]=[CH:11][C:10]([CH2:13][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6115AnilineHCID 103513-FuraldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18938795HCID 18938795, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of aniline (1.89 g, 19.6 mmol) and 3-furaldehyde (2.50 g, 26.8 mmol) in 1,2-dichloroethane (100 mL) under argon at 5° was treated with sodium triacetoxyborohydride (5.65 g, 26.8 mmol) and acetic acid (1.5 mL). The reaction mixture was stirred at room temperature overnight, concentrated in vacuo and the residue was diluted with ethyl acetate. The combined extracts were washed with satuirated sodium bicarbonate, dried over MgSO4 and concentrated. The product was purified by flash chromatography on silical gel (Hexane/EtOAc (20:1) to yield the title compound (3.31 g, 98%). Analysis calculated for C11H11NO: C, 76.28; H, 6.40; N, 8.09. Found: C, 76.58; H, 6.46; N, 8.33.

Workup

  1. concentrationconcentrated in vacuo
  2. additionthe residue was diluted with ethyl acetate
  3. washThe combined extracts were washed with satuirated sodium bicarbonate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography on silical gel (Hexane/EtOAc (20:1)

Sources & evidence

ORD record
ord-752244921fa34f97a22df1badd39c37c
Source dataset
uspto-grants-1998_11
Patent number
US05837702

Reaction notes

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