Furfural → HCID 68276449, compound

HRID 1400316Notes

Reaction equation

HRID 1400316 reaction equation
[Cl-].[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([Cl:13])=[C:8]([O:14][CH2:15][CH2:16][NH3+:17])[CH:7]=[CH:6]2.C([O-])([O-])=O.[K+].[K+].[O:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH:29]=O.[BH4-].[Na+]>CO>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([Cl:13])=[C:8]([O:14][CH2:15][CH2:16][NH:17][CH2:29][C:25]1[O:24][CH:28]=[CH:27][CH:26]=1)[CH:7]=[CH:6]2

Participants

6

Reactant 4

HCID 7362FurfuralHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 68276125HCID 68276125, compound

Product 1

HCID 68276449HCID 68276449, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[(6-bromo-1-chloronaphthalen-2-yl)oxy]ethanaminium chloride (91 mg, 0.27 mmol) in 10 mL of MeOH, K2CO3 (41 mg, 0.30 mmol) was added. After 10 min, 45 μL (0.54 mmol) of furan-2-carbaldehyde were added. The resulting solution was stirred for 1 h at room temperature, added with sodium borohydride (10 mg, 0.27 mmol) and then stirred for further 2 h at room temperature. The solvent was evaporated under vacuum and the crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH 95:5) to afford 2-[(6-bromo-1-chloronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)ethanamine as a brown solid (87 mg, 85% yield). 1H-NMR (DMSO-d6) δ: 8.35 (1H, d, J=2.05 Hz), 8.07 (1H, d, J=9.01 Hz), 8.00 (1H, d, J=9.01 Hz), 7.81 (1H, dd, J=1.05 Hz, J=2.08 Hz), 7.78 (1H, dd, J=2.05 Hz, J=8.98 Hz), 7.67 (1H, d, J=8.98 Hz), 6.70 (1H, dd, J=1.05 Hz, J=3.34 Hz), 6.34 (1H, dd, J=2.08 Hz, J=3.34 Hz), 4.55 (2H, d, J=5.44 Hz), 4.43 (2H, s), 3.43 (2H, d, J=5.44 Hz). HPLC-MS (ESI+): m/z 381.21 [M+H+].

Workup

  1. stirringstirred for further 2 h at room temperature
  2. customThe solvent was evaporated under vacuum
  3. customthe crude product was purified by flash chromatography on silica gel (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-7684929335c541f58aa91bf87cda4adb
Source dataset
uspto-grants-2014_12
Patent number
US08906946B2

Reaction notes

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