3-Furaldehyde → HCID 60208913, compound

HRID 1770461Notes

Reaction equation

HRID 1770461 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]=O)=[CH:2]1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH2:17])=[CH:12][CH:11]=1.[BH4-].[Na+]>CO>[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][NH:17][CH2:16][C:13]2[CH:14]=[CH:15][C:10]([O:9][CH3:8])=[CH:11][CH:12]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 103513-FuraldehydeHCID 754524-MethoxybenzylamineHCID 4311764Sodium borohydride

Product 1

HCID 60208913HCID 60208913, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-Furaldehyde (5 mmol, 437 μL) and (4-methoxyphenyl)methanamine in MeOH (20 mL) was stirred at ambient temperature overnight then sodium borohydride (300 mg, 7.89 mmol) was slowly added. The resulting mixture was stirred at room temperature for 15 minutes and quenched with NaOH (1 N, aq). Methanol was removed in vacuo and the resulting slurry was redissolved in ethyl acetate then, washed with water, brine, dried over sodium sulfate and concentrated. Purification by silica gel chromatography (Ethyl acetate:Hexanes 7:3) gave 1-(furan-3-yl)-N-(4-methoxybenzyl)methanamine as an oil. MS (M+H, 218.10); 1H NMR (400 MHz, CDCl3): δ, ppm: 3.64 (s, 2H), 3.74 (s, 2H), 3.80 (s, 3H), 6.39 (m, 1H), 6.86 (m, 1H), 6.88 (m, 1H), 7.23 (m, 1H), 7.25 (m, 1H), 7.35 (m, 1H), 7.38 (m, 1H).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 15 minutes
  2. customquenched with NaOH (1 N, aq)
  3. customMethanol was removed in vacuo
  4. dissolutionthe resulting slurry was redissolved in ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (Ethyl acetate:Hexanes 7:3)

Sources & evidence

ORD record
ord-2d5f854ee4e54fb4ac00589d832cbe4c
Source dataset
uspto-grants-2016_02
Patent number
US09247759B2

Reaction notes

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