(Trifluoromethyl)trimethylsilane → HCID 67403989, compound

HRID 1186392Notes

Reaction equation

HRID 1186392 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]=[O:10])[CH:2]=1.[F:11][C:12]([Si](C)(C)C)([F:14])[F:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:11][C:12]([F:14])([F:13])[CH:9]([OH:10])[CH2:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 111054123-(Pyridin-3-yl)propanal

Product 1

HCID 67403989HCID 67403989, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of 3-(pyridin-3-yl)propanal (180 mg, 1.3 mmol) obtained in Step 1 of Reference Example 8-64, (trifluoromethyl)trimethylsilane (0.24 mL, 1.6 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 0.27 mL, 0.27 mmol) and tetrahydrofuran (3.6 mL), the mixture was stirred and reacted at room temperature for 30 minutes. Then, purification by silica gel column chromatography (chloroform/methanol=1/0 to 10/1) was performed to give 1,1,1-trifluoro-4-(pyridin-3-yl)butan-2-ol (Compound EL) (83 mg, yield: 31%).

Workup

  1. customreacted at room temperature for 30 minutes
  2. customThen, purification by silica gel column chromatography (chloroform/methanol=1/0 to 10/1)

Sources & evidence

ORD record
ord-2259f5eba77641289810939ca3d27e24
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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