Methanol → 4-(2-Furanylmethoxy)benzenemethanamine

HRID 2080049Notes

Reaction equation

HRID 2080049 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7](#[N:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][OH:16].[Cl-].[NH4+].[O:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>O>[O:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[CH2:15][O:16][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][NH2:14])=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 7505BenzonitrileHCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 196273294-(2-Furanylmethoxy)benzenemethanamineYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Next, to a solution of lithium aluminum hydride (50 mg, 1.33 mmol) in tetrahydrofuran (1.0 mL) was added a solution of the resulting 4-furan-2-ylmethoxy)-benzonitrile (106 mg, 0.532 mmol) in tetrahydrofuran (1 mL) on an ice bath, and the solution was stirred at room temperature for 4 hours. A mixture solvent of methanol and water (9:1) was added to the reaction solution, an aqueous solution of saturated ammonium chloride was further added, the solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, then, the solvent was evaporated to obtain the title compound (76 mg, 70%) as a yellow solid.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ef706ab3ff3e44ba8817550e672c5cd3
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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