2-Methoxybenzaldehyde → HCID 53849990, compound

HRID 1386384Notes

Reaction equation

HRID 1386384 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:20](=O)[C:21]1[C:22]([O:27][CH3:28])=[CH:23][CH:24]=[CH:25][CH:26]=1>[OH-].[K+].CCO.O>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[C:14](=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH3:28])[CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 2

HCID 86582-MethoxybenzaldehydeHCID 154869126-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 53849990HCID 53849990, compoundYield 85.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

6-(2-Imidazole-1-yl-ethoxy)-3,4dihydro-2H-naphthalen-1-one (0.200 g, 0.78 mmol) was reacted with o-anisaldehyde (0.117 g, 0.87 mmol) in 2 mL of 4% KOH in EtOH at room temperature overnight. The reaction was diluted with water to induce the precipitation of a red gum. The aqueous layer was decanted, and the remaining residue was concentrated several times from EtOH and then chromatographed (SiO2, 30 g, 8% MeOH in DCM) to afford 0.249 g (84%) of the title compound as a yellow foam: APCI-MS m/e 375.3 (M++1).

Workup

  1. customthe precipitation of a red gum
  2. customThe aqueous layer was decanted
  3. concentrationthe remaining residue was concentrated several times from EtOH
  4. customchromatographed (SiO2, 30 g, 8% MeOH in DCM)

Sources & evidence

ORD record
ord-4540f509154b473880da8c4780e891da
Source dataset
uspto-grants-2001_07
Patent number
US06265422B1

Reaction notes

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