Hydrochloric Acid → (3,4-Dimethylthien-2-yl)-1-trityl-imidazol-4-yl-methanol

HRID 53906Notes

Reaction equation

HRID 53906 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]([C:10]1[N:11]=[CH:12][N:13]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=1)=[O:9].[BH4-].[Na+].Cl.C(=O)([O-])[O-].[Na+].[Na+]>CC(O)C>[CH3:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[CH:8]([C:10]1[N:11]=[CH:12][N:13]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=1)[OH:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 4311764Sodium borohydrideHCID 10551452(3,4-Dimethylthien-2-yl)-1-trityl-imidazol-4-yl methanone

Product 1

HCID 10551538(3,4-Dimethylthien-2-yl)-1-trityl-imidazol-4-yl-methanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of (3,4-dimethylthien-2-yl)-1-trityl-imidazol-4-yl methanone, C5, (3.4 g, 0.0075 mol) and sodium borohydride in 50 mL of 2-propanol was heated at reflux for 2 h. After cooling, 3N hydrochloric acid solution was added to the reaction mixture followed by 10% aqueous sodium carbonate solution. The mixture was concentrated under reduced pressure and the resulting solution was extracted twice with chloroform. The chloroform extracts were combined, dried (Na2SO4), and concentrated. The residue was recrystallized from ethyl acetate with a small amount of chloroform to give a white solid. The mother liquor was concentrated to give a second crop of the desired (3,4-dimethylthien-2-yl)-1-trityl-imidazol-4-yl-methanol, D5. The 1H NMR in CDCl3 supported the assigned structure. ##STR42##

Workup

  1. temperatureat reflux for 2 h
  2. temperatureAfter cooling
  3. concentrationThe mixture was concentrated under reduced pressure
  4. extractionthe resulting solution was extracted twice with chloroform
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate with a small amount of chloroform
  8. customto give a white solid
  9. concentrationThe mother liquor was concentrated

Sources & evidence

ORD record
ord-71114b16f5c14fd59bcc9b17d0708d18
Source dataset
uspto-grants-1997_04
Patent number
US05621113

Reaction notes

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