Ethyl Acetate → HCID 69039389, compound

HRID 397919Notes

Reaction equation

HRID 397919 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.[CH3:14][O:15][C:16]([C:18]1[N:19]=[CH:20][NH:21][CH:22]=1)=[O:17].CCOC(C)=O.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl>[CH3:14][O:15][C:16]([C:18]1[N:19]=[CH:20][N:21]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH:22]=1)=[O:17]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9357Potassium Sodium TartrateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 178418785HCID 178418785, compound

Product 1

HCID 69039389HCID 69039389, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of 2-naphtylboronic acid (1.4 g, 8 mmol), 1H-imidazole-4-carboxylic acid methyl ester (1.0 g, 8 mmol) and cupric acetate (1.4 g, 8 mmol) in CH2Cl2 (20 ml) was stirred at 20° C. for 24 h. AcOEt (100 ml) and saturated aqueous Seignette salt solution (50 ml) was added and the resulting mixture was stirred for another 2 h. After separation the organic phase was dried (Na2SO4), concentrated and chromatographed (silica, elution with CH2Cl2/MeOH 99:1) to yield the title compound (0.49 g, 24%) of the title compound as a white crystalline material. Mp. 143-144° C. (AcOEt), MS: m/e=252 (M+).

Workup

  1. stirringthe resulting mixture was stirred for another 2 h
  2. customAfter separation the organic phase
  3. dry with materialwas dried (Na2SO4)
  4. concentrationconcentrated
  5. customchromatographed
  6. wash(silica, elution with CH2Cl2/MeOH 99:1)

Sources & evidence

ORD record
ord-a8a17eda24c4453e9b3af1c2ae4c9681
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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