Triethylsilane → 4-[1-(tert-butyldimethylsilanyloxy)-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl]benzonitrile

HRID 1360141Notes

Reaction equation

HRID 1360141 reaction equation
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[Si:13]([O:20][CH:21]([C:50]1[CH:55]=[CH:54][C:53]([C:56]#[N:57])=[CH:52][CH:51]=1)[C:22]([O:24][CH2:25][C:26]1[N:27]=[CH:28][N:29]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=1)=O)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C([SiH](CC)CC)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Si:13]([O:20][CH:21]([C:50]1[CH:55]=[CH:54][C:53]([C:56]#[N:57])=[CH:52][CH:51]=1)[CH2:22][O:24][CH2:25][C:26]1[N:27]=[CH:28][N:29]([C:31]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=1)([C:16]([CH3:19])([CH3:17])[CH3:18])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 866329551-trityl-1H-imidazol-4-ylmethyl (tert-butyldimethylsilyloxy)(4-cyanophenyl)acetate

Product 1

HCID 667816954-[1-(tert-butyldimethylsilanyloxy)-2-(1-trityl-1H-imidazol-4-ylmethoxy)ethyl]benzonitrile

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1.27 mmol of titanium tetrachloride in 1.5 ml of dichloromethane is added to a solution of 2.61 mmol of trimethylsilyl trifluoromethanesulphonate in 1 ml of dichloromethane at 0° C. The mixture is stirred at room temperature for 4 hours and then cooled to 0° C. A solution of 0.83 mmol of 1-trityl-1H-imidazol-4-ylmethyl (tert-butyldimethylsilyloxy)(4-cyanophenyl)acetate and 4.17 mmol of triethylsilane in 2 ml of dichloromethane is added, and the reaction mixture is stirred at room temperature for 20 hours. The reaction mixture is poured into ice-water and extracted with ethyl acetate (2×). The combined organic phases are washed with water and brine; dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60F).

Workup

  1. temperaturecooled to 0° C
  2. stirringthe reaction mixture is stirred at room temperature for 20 hours
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined organic phases are washed with water and brine
  5. dry with materialdried with sodium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-f25d7b0bc0b34523bf7402519d97957a
Source dataset
uspto-grants-2011_02
Patent number
US07879847B2

Reaction notes

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