Acetic Acid → HCID 18778365, compound

HRID 576064Notes

Reaction equation

HRID 576064 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[CH:13]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[CH2:13][NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 97314-FluoroanilineHCID 691752,4-DimethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18778365HCID 18778365, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-fluoroaniline (3.85 g, 34.7 mmol) in tetrahydrofuran (100 mL) were added 2,4-dimethoxybenzaldehyde (6.34 g, 38.2 mmol) and acetic acid (11.9 mL, 208 mmol). After stirring at room temperature for 15 min, sodium triacetoxyborohydride (22.1 g, 104 mmol) was added thereto and the mixture was stirred at the same temperature for 15 hr. The mixture was concentrated under reduced pressure, diluted with ethyl acetate, and then washed with 2 mol/L aqueous sodium hydroxide solution and brine successively. The organic layer was dried over anhydrous sodium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to afford the title compound as a pale yellow solid (7.37 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 15 hr
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washwashed with 2 mol/L aqueous sodium hydroxide solution and brine successively
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationthe desiccant was filtered off
  7. concentrationfollowed by concentration under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-6fdf4c55d89443e9b699b6fc517fe243
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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