Triethylsilane → HCID 178460718, compound

HRID 498958Notes

Reaction equation

HRID 498958 reaction equation
[CH2:1]([S:4][C:5]1[CH:12]=[C:11]([C:13]2[C:14]([C:18]([F:21])([F:20])[F:19])=[N:15][NH:16][CH:17]=2)[CH:10]=[CH:9][C:6]=1[CH:7]=O)[CH2:2][CH3:3].C([SiH](CC)CC)C>C(Cl)Cl>[CH2:1]([S:4][C:5]1[CH:12]=[C:11]([C:13]2[C:14]([C:18]([F:20])([F:21])[F:19])=[N:15][NH:16][CH:17]=2)[CH:10]=[CH:9][C:6]=1[CH3:7])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 178460719HCID 178460719, compound

Product 1

HCID 178460718HCID 178460718, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.98 g (3.1 mmol) of 2-propylthio-4-(3-trifluoromethylpyrazolyl)benzaldehyde (Compound No. V-159 of the present invention) prepared in the same manner as in Example 8 (9) was dissolved in 10 ml of methylene chloride and stirred together with 1.44 g (12.4 mmol) of triethylsilane and 0.63 ml (6.8 mmol) of boron trifluoride diethyl ether complex at room temperature for 22 hours. The reaction mixture was poured into 50 ml of ice-cold water, and 20 ml of methylene chloride was added. The methylene chloride layer was separated, washed with 30 ml of water twice and dried over anhydrous magnesium sulfate, and the methylene chloride was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 0.18 g of [2-methyl-5-(3-trifluoromethylpyrazolyl)phenyl] propyl sulfide (yield 19.3%) as a colorless liquid (nD20 unmeasurable).

Workup

  1. additionwas added
  2. customThe methylene chloride layer was separated
  3. washwashed with 30 ml of water twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe methylene chloride was distilled off under reduced pressure
  6. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-17a3030862634d57bb69f729ebda794e
Source dataset
uspto-grants-2010_08
Patent number
US07767626B2

Reaction notes

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