Furfural → 2-[(1-chloronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)ethanamine

HRID 1400247Notes

Reaction equation

HRID 1400247 reaction equation
[Cl-].[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:13][CH2:14][CH2:15][NH3+:16].C([O-])([O-])=O.[K+].[K+].[O:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH:28]=O.[BH4-].[Na+]>CO>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:13][CH2:14][CH2:15][NH:16][CH2:28][C:24]1[O:23][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 7362FurfuralHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 681514342-[(1-Chloronaphthalen-2-yl)oxy]ethanaminium chloride

Product 1

HCID 29958842-[(1-chloronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)ethanamineYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[(1-chloronaphthalen-2-yl)oxy]ethanaminium chloride (100 mg, 0.39 mmol) in 10 mL of MeOH, K2CO3 (65 mg, 0.47 mmol) was added. After 10 min, 48 μL (0.58 mmol) of furan-2-carbaldehyde were added. The resulting solution was stirred for 1 h at room temperature, added with sodium borohydride (15 mg, 0.39 mmol) and the reaction was allowed to stir for further 2 h at room temperature. The solvent was evaporated under vacuum; the mixture was diluted with 10 mL CH2Cl2 and transferred to a separatory funnel. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH 95:5) to afford 2-[(1-chloronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)ethanamine as a brown oil (63% yield). The oil was left to stir with a 4M HCl dioxane solution for 1 h. The reaction mixture was concentrated under reduce pressure to afford 2-[(1-chloronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)ethanaminium chloride as a white solid.

Workup

  1. stirringto stir for further 2 h at room temperature
  2. customThe solvent was evaporated under vacuum
  3. additionthe mixture was diluted with 10 mL CH2Cl2
  4. customtransferred to a separatory funnel
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-7fc37c5b330342db935be9e6df402cf8
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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