Water → [2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetaldehyde

HRID 417166Notes

Reaction equation

HRID 417166 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:14][O:15]CC3CCCCC3)[C:11]3[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]([CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[CH:14]=[O:15])[C:11]3[CH:29]=[C:30]([F:34])[C:31]([F:33])=[CH:32][C:10]=3[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 666192022-(4-Chloro-phenyl)-1-(1-cyclohexyl-2-cyclohexylmethoxy-ethyl)-5,6-difluoro-1H-benzoimidazole2×

Product 1

HCID 86639904[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-cyclohexyl-acetaldehydeYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 200 mg (0.512 mmol) 2-[2-(4-chloro-phenyl)-benzoimidazol-1-yl]-2-cyclohexyl-ethanol (Ex. 1, intermediate c) in 2 ml dichloromethane was added 1.59 ml (2.17 g, 0.768 mmol) 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin-periodinane; 15 wt % in dichloromethane). The reaction mixture was stirred for 2 h at room temperature and then poured onto 30 ml dichloromethane and 30 ml water. The aqueous layer were extracted again with 30 ml dichloromethane. The combined organic layers were washed with 30 ml brine, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by silica chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 60:40) to give the product as a colorless solid (74%). MS (Turbo Spray): m/z=389.2 [M+H].

Workup

  1. extractionThe aqueous layer were extracted again with 30 ml dichloromethane
  2. washThe combined organic layers were washed with 30 ml brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by silica chromatography
  7. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 60:40)

Sources & evidence

ORD record
ord-ab417e393fcc442faacdb3c55c6a533a
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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