Pyridine → 2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

HRID 1441128Notes

Reaction equation

HRID 1441128 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[CH3:10][C:11]1[CH:12]=CC(C)=[CH:15][CH:16]=1.O1CCOC1.N1C=CC=CC=1>C(OCC)(=O)C>[CH3:10][C:11]1([CH3:12])[CH:16]=[CH:15][C:5]2[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][C:6]=2[O:9]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7809P-XyleneHCID 125861,3-DioxolaneHCID 130194-Cyanophenol

Product 1

HCID 27790742,2-dimethyl-2H-1-benzopyran-6-carbonitrileYield 30%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

Under an argon atmosphere, 4-cyanophenol (0.186 g, 1.56 mmole), p-xylene (1 mL), the dioxolane prepared above (0.2 g, 1.56 mmole), and pyridine (0.12 mL, 1.56 mmole) were combined in that order. The mixture was heated to 140° C. (internal temperature). After 24 hours, the reaction mixture was diluted with ethyl acetate (3 mL) and washed with 10% hydrochloric acid. The organic layers were collected, washed with 1N sodium hydroxide, brine, dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a dark brown oil (0.085 g, 30% yield).

Workup

  1. washwashed with 10% hydrochloric acid
  2. customThe organic layers were collected
  3. washwashed with 1N sodium hydroxide, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71f431399b6c47888cff09e787275aa3
Source dataset
uspto-grants-1996_03
Patent number
US05502220

Reaction notes

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