Triethylsilane → HCID 178460718, compound

HRID 1635734Notes

Reaction equation

HRID 1635734 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>[CH3:7][C:6]1[CH:9]=[CH:10][C:11]([C:13]2[C:14]([C:18]([F:21])([F:19])[F:20])=[N:15][NH:16][CH:17]=2)=[CH:12][C:5]=1[S:4][CH2:1][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 (nD2 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-f0742cf48b1943008f3d88dd2dac4b06
Source dataset
uspto-grants-2003_01
Patent number
US06509354B1

Reaction notes

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