1,1-Dichloroethane → 3-[(S)-[1-(2-methylphenyl)imidazol-2-yl]sulfinyl]propan-1-ol

HRID 1736403Notes

Reaction equation

HRID 1736403 reaction equation
ClC(Cl)C.[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[S:17][CH2:18][CH2:19][CH2:20][OH:21].[O-:22]O.C1(C(C)C)C=CC=CC=1>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[S@:17]([CH2:18][CH2:19][CH2:20][OH:21])=[O:22]

Participants

5

Reactant 3

HCID 63651,1-DichloroethaneHCID 108578301-Propanol, 3-[[1-(2-methylphenyl)-1H-imidazol-2-yl]thio]-HCID 53627471Cumen hydroperoxide

Product 1

HCID 111082223-[(S)-[1-(2-methylphenyl)imidazol-2-yl]sulfinyl]propan-1-olYield 38.2%

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

To 3 l of dichloroethane were added 123 g of 3-[1-(2-methylphenyl)-2-imidazolylthio]propanol, 414 g of L-(+)-diethyl tartarate and 120 g of a powder of Molecular Sieve 4A. The mixture was stirred at room temperature for 2 days. Thereto was added 142 g of titanium tetraisopropoxide. The mixture was stirred at room temperature for 30 minutes. Thereto was added 91 g of cumene hydroperoxide. The mixture was stirred at 5° C. for 24 hours. The reaction mixture per se was purified by a silica gel column chromatography (eluant: dichloromethane/methanol=50/1). Recrystallization from methyl ethyl ketone was repeated to obtain 50 g of (S)-(+)-3-[1-(2-methylphenyl)2-imidazolylsulfinyl]propanol.

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. stirringThe mixture was stirred at 5° C. for 24 hours
  3. customThe reaction mixture per se was purified by a silica gel column chromatography (eluant: dichloromethane/methanol=50/1)
  4. customRecrystallization from methyl ethyl ketone

Sources & evidence

ORD record
ord-ac77a5315f964bf5aac81587e400099f
Source dataset
uspto-grants-1996_07
Patent number
US05541198

Reaction notes

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