Lithium Hexamethyldisilazide → HCID 67322357, compound

HRID 1875853Notes

Reaction equation

HRID 1875853 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH2:9][S:10][CH3:11])=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].N1([C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])C=CN=C1>CC(OC)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:12])[CH:9]([S:10][CH3:11])[C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 12623182HCID 12623182, compoundHCID 143730331-(4-Chlorophenyl)-2-(methylsulfanyl)ethan-1-one

Product 1

HCID 67322357HCID 67322357, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

To a solution of 15 g of 1-(4-chlorophenyl)-2-(methylthio)ethanone (2) in 70 mL of MTBE is added a solution of 86 mL of lithium hexamethyldisilazide (LiHMDS) under nitrogen gas, while keeping the temperature at −40° C. After stirring for 1.5 hours at this temperature, 14.4 g of ethyl 2-(1H-imidazol-1-yl)-2-oxoacetate (3) in 50 mL MTBE are added at 0° C., and the mixture is left stirring overnight at room temperature. The reaction solution was filtered off and the filtrate was suspended in 80 mL of MTBE. 50 mL of 6N HCl are added to the suspension. After separation of the phase by settling, the ether phase is washed 4 times with water and then concentrated under reduced pressure to obtain 22 g (73 mmol) of the title compound.

Workup

  1. customat −40° C
  2. additionare added at 0° C.
  3. waitthe mixture is left
  4. filtrationThe reaction solution was filtered off
  5. addition50 mL of 6N HCl are added to the suspension
  6. customAfter separation of the phase
  7. washthe ether phase is washed 4 times with water
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e806658569b4045903cacb9e8f8cca7
Source dataset
uspto-grants-2012_11
Patent number
US08309584B2

Reaction notes

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