Methanol → HCID 178515661, compound

HRID 1859792Notes

Reaction equation

HRID 1859792 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][CH:29]=[C:28]1[CH:32]=O.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:28]2[S:27][CH:31]=[CH:30][CH:29]=2)[CH2:20][CH2:19]3)[N:10]=[CH:9]1

Participants

7

Reactant 3

HCID 887MethanolHCID 73642-ThiophenecarboxaldehydeHCID 54451574HCID 54451574, compound

Product 1

HCID 178515661HCID 178515661, compoundYield 43.9%

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 (0.356,g, 1.0 mmol) was reacted with thiophene-2-carboxaldehyde (0.174 g, 1.55 mmol) in 5 mL of 4% KOH in EtOH for 24 hours to afford, after chromatography (silica gel, 60 g; 8% MeOH in DCM), 0.154 g (40%) of the title compound as a red glassy solid, mp 60-63° C.: CI-MS m/e 351 (M++1).

Workup

  1. customto afford

Sources & evidence

ORD record
ord-74e3ac6618c345b5be0b5b1b6e6cb590
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

Loading…