Water → HCID 22130474, compound

HRID 1416034Notes

Reaction equation

HRID 1416034 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:11]([CH3:27])[C:12]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)=[C:13]([CH:15]([CH3:18])[C:16]#[N:17])[N:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O>O1CCCC1>[Cl:26][C:22]1[CH:21]=[C:20]([S:19][C:12]2[N:11]([CH3:27])[C:10]([CH2:9][OH:8])=[N:14][C:13]=2[CH:15]([CH3:18])[C:16]#[N:17])[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 22130402HCID 22130402, compound

Product 1

HCID 22130474HCID 22130474, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In dry tetrahydrofuran (2 ml)was dissolved 70 mg of 2-(2-t-butyldimethylsilyloxymethyl-5-(3-chlorophenylthio)-1-methyl-1H-imidazol-4-yl)propiononitrile (50'), followed by addition of 0.33 ml of 1 M tetrabutylammoniumfluoride-tetrahydrofuran solution, and the reaction mixture was stirred at room temperature for 10 minutes. To the reaction mixture, water was added, extracted with methylene chloride, the organic layer was washed with water and dried over sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate)to obtain 50 mg of 2-[5-(3-chlorophenylthio)-2-hydroxymethyl-1-methyl-1H-imidazol-4-yl]propiononitrile (50) as oil (yield 98%).

Workup

  1. extractionextracted with methylene chloride
  2. washthe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (ethyl acetate)to

Sources & evidence

ORD record
ord-cccd245f81584c8284fd329a274704be
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

Loading…