3-Furaldehyde → HCID 60208913, compound

HRID 658625Notes

Reaction equation

HRID 658625 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 1.5 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 1.5 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-914e4df7f35b4fb982c0e13c92753f10
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

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