Tetrahydrofuran → HCID 62395749, compound

HRID 1428702Notes

Reaction equation

HRID 1428702 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:8]=[CH:9][CH:10]=1)#[N:4].O1CCC[CH2:17]1>>[C:3]([C:5]1[CH:6]=[C:7]([CH:11]([CH3:17])[C:12]([O:14][CH3:15])=[O:13])[CH:8]=[CH:9][CH:10]=1)#[N:4]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 1514291Methyl (3-cyanophenyl)acetate

Product 1

HCID 62395749HCID 62395749, compoundYield 48%

Procedure

To the cooled solution of sodium hydride (91 mg, 2.285 mmol, 60% suspension in oil) in anhydrous tetrahydrofuran was added a solution of methyl 2-(3-cyanophenyl)acetate (400 mg, 2.285 mmol) dropwise at 0° C. Reaction mixture was stirred at room temperature for 1 h. TLC showed complete consumption of starting material. The reaction mixture was quenched with brine and extracted with ethyl acetate. The organic part was washed with brine and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford crude product which was purified by column chromatography to afford methyl 2-(3-cyanophenyl)propanoate (180 mg, 48%).

Workup

  1. customReaction mixture
  2. customconsumption of starting material
  3. customThe reaction mixture was quenched with brine
  4. extractionextracted with ethyl acetate
  5. washThe organic part was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto afford crude product which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b5cac48406134f7c9f34dab8f787b265
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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