Reaction #586140

Reaction equation

2-propylthio-4-(3-trifluoromethylpyrazolyl)benzaldehyde

triethylsilane

→

[2-methyl-5-(3-trifluoromethylpyrazolyl)phenyl] propyl sulfide

Yield 19.3%

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   OtherThe methylene chloride layer was separated
3. 3
   Washwashed with 30 ml of water twice
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe methylene chloride was distilled off under reduced pressure
6. 6
   OtherPurification of the residue by silica gel column chromatography

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).

Source