m-Formylbenzonitrile → HCID 61645255, compound

HRID 1186347Notes

Reaction equation

HRID 1186347 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7])=[O:2].[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:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[C:6]#[N:7])[OH:2]

Participants

5

Reactant 3

HCID 90670m-FormylbenzonitrileHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 61645255HCID 61645255, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of 3-formylbenzonitrile (500 mg, 3.81 mmol), (trifluoromethyl)trimethylsilane (678 μL, 4.58 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 381 μL, 0.381 mmol) and tetrahydrofuran (10 mL), the mixture was stirred and reacted at room temperature for 3 hours. Then, purification by silica gel column chromatography (hexane/ethyl acetate=7/3) was performed to give 3-(2,2,2-trifluoro-1-hydroxyethyl)benzonitrile (Compound CZ) (705 mg, yield: 92%).

Workup

  1. customreacted at room temperature for 3 hours
  2. customThen, purification by silica gel column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-cb882d5801e54c1ea0f0607cdf178a28
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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