Sodium Hydroxide → HCID 178437184, compound

HRID 747281Notes

Reaction equation

HRID 747281 reaction equation
[C:1]1([C:11]([C:14]2[N:15]=[CH:16][N:17](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:18]=2)(O)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)(=O)C.O>[C:1]1([C:11]([C:14]2[N:15]=[CH:16][NH:17][CH:18]=2)=[CH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10552746HCID 10552746, compound

Product 1

HCID 178437184HCID 178437184, compound

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

1-Naphthalen-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate H1) in acetic acid:water (˜2:1) was heated to 100° C. for 1 h. The mixture was basified with 1 M NaOH and extracted (6×) with CHCl3:iPrOH (3:1). The organic solution was dried over MgSO4, filtered, and concentrated onto silica gel. The material was eluted from a column of silica with 5% NH3-MeOH:CH2Cl2 to give 4-(1-naphthalen-1-yl-vinyl)-1H-imidazole.

Workup

  1. extractionextracted (6×) with CHCl3:iPrOH (3:1)
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated onto silica gel
  5. washThe material was eluted from a column of silica with 5% NH3-MeOH

Sources & evidence

ORD record
ord-9085c7176d8944608a209078e7810576
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

Loading…