(Trifluoromethyl)trimethylsilane → HCID 68814927, compound

HRID 732568Notes

Reaction equation

HRID 732568 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2].C[Si](C)(C)[C:23]([F:26])([F:25])[F:24].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH:18]([OH:19])[C:23]([F:26])([F:25])[F:24])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 86615013HCID 86615013, compound

Product 1

HCID 68814927HCID 68814927, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Treat a solution of 5-formyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (500 mg, 1.8 mmol) in THF (10 mL) at 0° C. with trimethyl(trifluoromethyl)silane (0.5 M in THF, 5.4 mL, 2.70 mmol) and tetrabutylammonium fluoride (1.0 M in THF, 2.7 mL, 2.70 mmol). Stir at 0° C. for 2 h and quench with saturated aqueous NaHCO3. Extract with ethyl acetate (100 mL), dry (magnesium sulfate) and concentrate to give the crude title product which is used in the next step without further purification.

Workup

  1. customquench with saturated aqueous NaHCO3
  2. extractionExtract with ethyl acetate (100 mL)
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-442bf1d5ccd548c795ec28a8b39f1388
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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