Water → 2-[4-(4-Fluorophenyl)oxan-4-yl]acetonitrile

HRID 626472Notes

Reaction equation

HRID 626472 reaction equation
[OH-].[K+].[C:3]([CH:5]([C:10]1([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)C(OC)=O)#[N:4].O>C(O)CO>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:10]2([CH2:5][C:3]#[N:4])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 68314247HCID 68314247, compound

Product 1

HCID 683143362-[4-(4-Fluorophenyl)oxan-4-yl]acetonitrile

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
120 °C

Procedure

To a pre-dissolved solution of KOH (441 mg, 7.87 mmol) in ethylene glycol (20 ml) was added methyl 2-cyano-2-[4-(4-fluorophenyl)oxan-4-yl]acetate (1.09 g, 3.93 mmol). The mixture was heated to 120° C. for 3 h, and then cooled. H2O was added (50 ml), the product extracted with Et2O (3×50 ml), washed with H2O (50 ml), dried over NA2SO4, filtered and concentrated. Purified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes) to give 2-[4-(4-fluorophenyl)oxan-4-yl]acetonitrile as a colorless oil (450 mg, 78%, m/z: 219.1 [M+H]+ observed).

Workup

  1. temperaturecooled
  2. extractionthe product extracted with Et2O (3×50 ml)
  3. washwashed with H2O (50 ml)
  4. customdried over NA2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4d567f157aea4ba58904d7df8510ebdf
Source dataset
uspto-grants-2016_04
Patent number
US09309234B2

Reaction notes

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