Methanol → 849805-97-6

HRID 2080048Notes

Reaction equation

HRID 2080048 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16].CO.[Cl-].[NH4+]>O1CCCC1.O>[F:7][C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[O:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][NH2:16]

Participants

7

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 23130454849811-45-6

Product 1

HCID 23130480849805-97-6Yield 89.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Next, to a solution of lithium aluminum hydride (139 mg, 3.68 mmol) in tetrahydrofuran (3.0 mL) was added a solution of the resulting 3-(3-fluoro-phenoxy)-benzonitrile (313 mg, 1.47 mmol) in tetrahydrofuran (1 mL) on an ice bath, and the solution was stirred at room temperature for 18 hours. A mixture solvent of methanol and water (9:1) was added to the reaction solution, an aqueous solution of saturated ammonium chloride was further added thereto, followed by stirring at room temperature for 10 minutes, then, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, then, the solvent was evaporated to obtain the title compound (285 mg, 89%) as a yellow oil.

Workup

  1. stirringby stirring at room temperature for 10 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cd891cc4cd594e589429508263fbef33
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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