2-Thiophenecarboxaldehyde → HCID 53956948, compound

HRID 368308Notes

Reaction equation

HRID 368308 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.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH:25]=O>[OH-].[K+].CCO>[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:25][C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 73642-ThiophenecarboxaldehydeHCID 154869126-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 53956948HCID 53956948, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

According to the method of Example 8, 6-(2-imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (0.400 g, 1.56 mmol) was reacted with 2-thiophene carboxaldehyde (0.264 g, 2.35 mmol) in 5.0 mL of 4% KOH in EtOH for 4.5 hours at room temperature to afford 0.369 g (67%) of the title compound as dark yellow crystals, mp 137-138° C.: CI-MS m/e 350 (M+), 351 (M+ +1); 1H-NMR (CDCl3): δ 8.04 (1H, d, J=8.6 Hz), 7.98 (1H, s), 7.59 (1H, s), 7.47 (1H, d, J=4.9 Hz), 7.34 (1H, d, J=3.4 Hz), 7.10 (1H, m), 7.05 (1H, s), 7.01 (1H, s), 6.80 (1H, dd, J=8.6 Hz, J=2.4 Hz), 6.67 (1H, br s), 4.34 (2H, m), 4.25 (2H, m), 3.15 (2H, m), 2.94 (2H, m).

Sources & evidence

ORD record
ord-2ad35895d937402b815ad3e22bbf9eda
Source dataset
uspto-grants-2000_10
Patent number
US06133303

Reaction notes

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