5-(Methylsulfanyl)thiophene-2-carbaldehyde → 6-(2-Imidazole-1-yl-ethoxy)-2-(5-methylsulfanyl-thiophen-2-ylmethylene)-3,4-dihydro-2H-naphthalen-1-one

HRID 368313Notes

Reaction equation

HRID 368313 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.[CH3:20][S:21][C:22]1[S:26][C:25]([CH:27]=O)=[CH:24][CH:23]=1>[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:27][C:25]2[S:26][C:22]([S:21][CH3:20])=[CH:23][CH:24]=2)[CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 27369975-(Methylsulfanyl)thiophene-2-carbaldehydeHCID 154869126-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 543820576-(2-Imidazole-1-yl-ethoxy)-2-(5-methylsulfanyl-thiophen-2-ylmethylene)-3,4-dihydro-2H-naphthalen-1-oneYield 75.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

According to the method of Example 4, 6-(2-imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (0.25 g, 0.98 mmol) was reacted with 5-(methylthio)thiophene-2-carboxaldehyde (0.233 g, 1.47 mmol) in 4 mL of 4% KOH in EtOH for 2 hours at room temperature to afford 0.293 g (36%) of the title compound as a dark yellow powder, mp 102-104° C.: APCI-MS m/e 397.5 (M+ +1).

Sources & evidence

ORD record
ord-316b9fdc3e77492fa1bf4b790306ac7f
Source dataset
uspto-grants-2000_10
Patent number
US06133303

Reaction notes

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