Methanol → HCID 178515709, compound

HRID 1386387Notes

Reaction equation

HRID 1386387 reaction equation
C(OC([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:25]=[CH:24][C:23]3[C:22](=[O:26])[CH2:21][CH2:20][CH2:19][C:18]=3[CH:17]=2)[N:10]=[CH:9]1)=O)(C)(C)C.[S:27]1[CH:31]=[CH:30][C:29]([CH:32]=O)=[CH:28]1.CO>[OH-].[K+].CCO.C(Cl)Cl>[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[C:22](=[O:26])[C:21](=[CH:32][C:29]2[CH:30]=[CH:31][S:27][CH:28]=2)[CH2:20][CH2:19]3)[N:10]=[CH:9]1

Participants

7

Reactant 3

HCID 887MethanolHCID 681353-ThiophenecarboxaldehydeHCID 54451574HCID 54451574, compound

Product 1

HCID 178515709HCID 178515709, compoundYield 62.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 14797Potassium HydroxideSolvent

Procedure

According to the method of Example 32, Step 2, 4-[2-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yloxy)-ethyl]-imidazole-1-carboxylic acid tert-butyl ester (0.270 g, 0.76 mmol) was reacted with thiophene-3-carboxaldehyde (0.128 g, 1.14 mmol) in 5 mL of 4% KOH in EtOH for 22 hours to afford, after chromatography (silica gel, 50 g; 8% MeOH in DCM), 0.167 g (59%) of the title compound as a dull yellow powder, mp 94-96° C.: CI-MS m/e 351 (M++1).

Workup

  1. customto afford

Sources & evidence

ORD record
ord-0147af8df5624bd19849bc94dcef0ac1
Source dataset
uspto-grants-2001_07
Patent number
US06265422B1

Reaction notes

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