4-(2-(Diethylamino)-Ethoxy)-Benzaldehyde → 2-[4-(2-Diethylamino-ethoxy)-benzylidene]-6-(2-imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

HRID 1859774Notes

Reaction equation

HRID 1859774 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.[CH2:20]([N:22]([CH2:25][CH2:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)[CH2:23][CH3:24])[CH3:21]>[OH-].[K+].[Cl-].[Na+].O>[CH2:23]([N:22]([CH2:20][CH3:21])[CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([CH:32]=[C:14]2[CH2:13][CH2:12][C:11]3[C:16](=[CH:17][CH:18]=[C:9]([O:8][CH2:7][CH2:6][N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)[CH:10]=3)[C:15]2=[O:19])=[CH:34][CH:35]=1)[CH3:24]

Participants

5

Reactant 2

HCID 4116744-(2-(Diethylamino)-Ethoxy)-BenzaldehydeHCID 15486912HCID 15486912, compound

Product 1

HCID 540331082-[4-(2-Diethylamino-ethoxy)-benzylidene]-6-(2-imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-oneYield 30.3%

Reagents, catalysts & solvents 2

HCID 14797Potassium HydroxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

6-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (0.505 g, 1.97 mmol) was reacted with 4-(diethylamino)ethoxy benzaldehyde (0.662 g, 3.0 mmol) in 2.5 mL of 4% KOH for 20 hours at room temperature. The reaction was diluted with brine, and the resulting mixture was extracted into DCM. The combined extracts were dried, filtered, and evaporated to dryness. The resulting oil was purified twice by flash chromatography (silica gel, 150 g, 10% MeOH in DCM) to afford 0.274 g (30%) of the title compound as a yellow oil: CI-MS m/e 459 (M+), 460 M++1);

Workup

  1. extractionthe resulting mixture was extracted into DCM
  2. customThe combined extracts were dried
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe resulting oil was purified twice by flash chromatography (silica gel, 150 g, 10% MeOH in DCM)

Sources & evidence

ORD record
ord-d3f9b673ae894c8d987e24ba59d6e231
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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