Trifluoroacetic acid → HCID 14329267, compound

HRID 727864Notes

Reaction equation

HRID 727864 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=[C:17]2[S:22][CH2:21][S:20][CH2:19][S:18]2)[CH2:15][CH3:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH:17]2[S:18][CH2:19][S:20][CH2:21][S:22]2)[CH2:15][CH3:16])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 14329340HCID 14329340, compound

Product 1

HCID 14329267HCID 14329267, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 10 ml of anhydrous dichloromethane were dissolved 1.0 g of 2-{1-(4-phenoxyphenyl)propan-1-ylidene}-1,3,5-trithiane and 0.67 g of triethylsilane, and a solution prepared by diluting 1 ml of trifluoroacetic acid with 5 ml of dichloromethane was added dropwise at room temperature. The resulting solution was stirred overnight. After sodium carbonate powder was added, the resulting mixture was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation, and then the residue was purified by a silica gel column chromatography (chloroform:hexane=2:1) to give 0.91 g of the desired compound.

Workup

  1. customa solution prepared
  2. additionwas added dropwise at room temperature
  3. washthe resulting mixture was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation
  6. customthe residue was purified by a silica gel column chromatography (chloroform:hexane=2:1)

Sources & evidence

ORD record
ord-2725c175e0884e7c94867777e02e9374
Source dataset
uspto-grants-1991_09
Patent number
US05045562

Reaction notes

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