Triethylsilane → HCID 66915588, compound

HRID 656483Notes

Reaction equation

HRID 656483 reaction equation
FC(F)(F)S(OO[Si](C)(C)C)(=O)=O.[CH3:14][O:15][C:16]1[CH:21]=[C:20]2[O:22][C:23](=O)[CH2:24][C:25]3([CH2:30][CH2:29][CH2:28][N:27]4[CH:31]=[N:32][CH:33]=[C:26]34)[C:19]2=[CH:18][CH:17]=1.C([SiH](CC)CC)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:14][O:15][C:16]1[CH:21]=[C:20]2[O:22][CH2:23][CH2:24][C:25]3([CH2:30][CH2:29][CH2:28][N:27]4[CH:31]=[N:32][CH:33]=[C:26]34)[C:19]2=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 12052TriethylsilaneHCID 18921935HCID 18921935, compoundHCID 66915646HCID 66915646, compound

Product 1

HCID 66915588HCID 66915588, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

A solution of 2.61 mmol of trimethylsilyloxy trifluoromethanesulphonate in 1 ml of dichloro-methane at 0° C. is admixed with a solution of 1.27 mmol of titanium tetrachloride in 1.5 ml of dichloromethane. The mixture is stirred at room temperature for 4 hours and then cooled to 0° C. A solution of 0.83 mmol of 7-methoxy-6′,7′-dihydro-5′H-spiro[chromene-4,8′-imidazo[1,5-a]pyridin]-2(3H)-one 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. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

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

Sources & evidence

ORD record
ord-609d2b85025e42928b1b8d673e934751
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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