Furfural → HCID 59596837, compound

HRID 2264663Notes

Reaction equation

HRID 2264663 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[F:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][NH2:22])[CH:17]=[CH:18][CH:19]=1.[BH4-].[Na+]>C(O)C>[F:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[CH2:12][O:13][C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][NH:22][CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7362FurfuralHCID 4311764Sodium borohydrideHCID 236253522-[3-(3-Fluoro-benzyloxy)-phenyl]-ethylamine

Product 1

HCID 59596837HCID 59596837, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

1.44 g (15 mmol) of furan-2-carboxaldehyde and 7.5 g of molecular sieves 3 Å were added to a solution of 2.45 g (10 mmol) of 2-[3-(3-fluoro-benzyloxy)-phenyl]-ethylamine in 50 ml of dry ethanol. The reaction mixture was refluxed for 3 hours. The molecular sieves were filtered off and the solution was cooled to 5° C. 0.57 g (15 mmol) of NaBH4 was added under N2 and the reaction was stirred at room temperature overnight. Solvent was removed, a 5% NaHCO3 aqueous solution was added to the residue and the product was extracted with ethyl acetate. The crude product was purified by flash chromatography (dichloromethane/methanol/NH3 100:0:0→100:2:0.2, v:v:v). 2.2 g (68% yield) of an oil were obtained.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. filtrationThe molecular sieves were filtered off
  3. customSolvent was removed
  4. additiona 5% NaHCO3 aqueous solution was added to the residue
  5. extractionthe product was extracted with ethyl acetate
  6. customThe crude product was purified by flash chromatography (dichloromethane/methanol/NH3 100:0:0→100:2:0.2, v:v:v)

Sources & evidence

ORD record
ord-7d604f1473fb4a358399c4b3e8c80ca1
Source dataset
uspto-grants-2010_12
Patent number
US07855227B2

Reaction notes

Loading…