Water → 1-(3-Fluorophenyl)-4-oxocyclohexanecarbonitrile

HRID 45185Notes

Reaction equation

HRID 45185 reaction equation
[C:1]([C:3]1([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH:5](C(OC)=O)[CH2:4]1)#[N:2].O>CS(C)=O>[C:1]([C:3]1([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 962WaterHCID 58380928HCID 58380928, compound

Product 1

HCID 214336191-(3-Fluorophenyl)-4-oxocyclohexanecarbonitrileYield 69.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 1-cyano-1-(3-fluorophenyl)-3-methoxycarbonylcyclohexan-4-one (57, 51 g, 185 mmol), water (54.8 mL) and DMSO (840 mL) was heated and stirred at 150° C. for 3 hours, followed by stirring at room temperature overnight. The reaction mixture was evaporated and purified by chromatography on silica gel. Elution with ethyl acetate/heptane (5%:95% to 30%:70%) gave 28 g of desired material as a solid product. Rt=3.89 min (Method 3). Detected mass: 218.2 (M+H+).

Workup

  1. temperaturewas heated
  2. stirringby stirring at room temperature overnight
  3. customThe reaction mixture was evaporated
  4. custompurified by chromatography on silica gel
  5. washElution with ethyl acetate/heptane (5%:95% to 30%:70%)

Sources & evidence

ORD record
ord-c826da8d534e40158cc0e144bb4304b5
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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