Sodium borohydride → 2-(1,3-dihydrobenzimidazol-2-ylidene)-1-[3-(1,3-dihydroxybutyl)phenyl]-3-(3-fluorophenyl)propane-1,3-dione

HRID 658112Notes

Reaction equation

HRID 658112 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([OH:33])[CH2:29][C:30](=[O:32])[CH3:31])[CH:23]=1)=[O:21])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=[O:12].[BH4-].[Na+]>C(O)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)=[O:12])[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]([OH:33])[CH2:29][CH:30]([OH:32])[CH3:31])[CH:23]=1)=[O:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178467978HCID 178467978, compound

Product 1

HCID 1784679792-(1,3-dihydrobenzimidazol-2-ylidene)-1-[3-(1,3-dihydroxybutyl)phenyl]-3-(3-fluorophenyl)propane-1,3-dioneYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

At −10° C., 10 ml of ethanol solution containing 184 mg of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-(3-fluorophenyl)-3-[3-(1-hydroxy-3-oxobutyl)phenyl]propane-1,3-dione was mixed with sodium borohydride and stirred for 30 minutes. This was appropriate amounts of saturated ammonium chloride aqueous solution and purified water, extracted with ethyl acetate and dried with anhydrous magnesium sulfate. After concentration, the thus formed residue was purified by a silica gel column chromatography to obtain 110 mg (60%) of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-[3-(1,3-dihydroxybutyl)phenyl]-3-(3-fluorophenyl)propane-1,3-dione (Example 6-1) from a hexane-ethyl acetate (1:1-1:3) eluate.

Workup

  1. customThis was appropriate amounts of saturated ammonium chloride aqueous solution and purified water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationAfter concentration
  5. customthe thus formed residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-9ef307c842524726a1060a141d389b93
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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