HCID 67026311, compound → HCID 67026311, compound

HRID 907514Notes

Reaction equation

HRID 907514 reaction equation
[CH3:1][C:2]1[N:6]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5](C(C2C3C(=CC=CC=3)C=CC=2)(O)C)=[N:4][CH:3]=1.[CH3:39][C:40]1[N:41]=[CH:42][N:43]([C:58]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)[C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C:44]=1[C:45]([C:48]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=[CH:50][CH:49]=1)([OH:47])[CH3:46].CC1N=CN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=1C(C1C2C(=CC=CC=2)C=CC=1)=O.C[Mg]Br>ClCCl>[CH3:1][C:2]1[N:6]([C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:5]=[N:4][C:3]=1[C:45]([C:48]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=[CH:50][CH:49]=1)([OH:47])[CH3:44].[CH3:39][C:40]1[N:41]=[CH:42][N:43]([C:58]([C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)([C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)[C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)[C:44]=1[C:45]([C:48]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=[CH:50][CH:49]=1)([OH:47])[CH3:46]

Participants

7

Reactant 4

HCID 67026311HCID 67026311, compoundHCID 67026528HCID 67026528, compoundHCID 67413316HCID 67413316, compoundHCID 178418573HCID 178418573, compound

Product 2

HCID 67026279HCID 67026279, compoundHCID 67026311HCID 67026311, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(5-Methyl-1-trityl-1H-imidazolyl)-1-(naphthalen-1-yl)ethanol and 1-(4-methyl-1-trityl-1H-imidazol-5-yl)-1-(naphthalen-1-yl)ethanol (12): A solution of (11) (1.33 g, 2.78 mmol) in dichloromethane (50 mL) at 0° C. was added methyl magnesium bromide (3.0 M in diethyl ether, 1.85 mL, 5.50 mmol) drop wise. The reaction mixture was warmed to room temperature over night. The mixture was quenched with ammonium chloride (aq). The resulting aqueous layer was extracted with chloroform three times (200 mL). The pooled organic layers were dried over magnesium sulfate. The mixture was filtered, and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 50% hexane and 50% ethyl acetate to give 1-(5-methyl-1-trityl-1H-imidazol-4-yl)-1-(naphthalen-1-yl)ethanol and 1-(4-methyl-1-trityl-1H-imidazol-5-yl)-1-(naphthalen-1-yl)ethanol (12) (1.21 g, 2.45 mmol, 88% yield).

Workup

  1. customThe mixture was quenched with ammonium chloride (aq)
  2. extractionThe resulting aqueous layer was extracted with chloroform three times (200 mL)
  3. dry with materialThe pooled organic layers were dried over magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customthe solvents were removed under vacuum
  6. customThe residue was purified by chromatography on silica gel with 50% hexane and 50% ethyl acetate

Sources & evidence

ORD record
ord-c1b725ab953e4d4d84b00358346c98c2
Source dataset
uspto-grants-2011_09
Patent number
US08013169B2

Reaction notes

Loading…