HCID 89600898, compound → 2,5,5-Trimethylcyclopent-1-ene-1-carbonitrile

HRID 530238Notes

Reaction equation

HRID 530238 reaction equation
O[C:2]1([C:10]#[N:11])[CH:6]([CH3:7])[CH2:5][CH2:4][C:3]1([CH3:9])[CH3:8]>S(Cl)(Cl)=O>[CH3:7][C:6]1[CH2:5][CH2:4][C:3]([CH3:9])([CH3:8])[C:2]=1[C:10]#[N:11]

Participants

3

Reactant 1

HCID 89600898HCID 89600898, compound

Product 1

HCID 217652822,5,5-Trimethylcyclopent-1-ene-1-carbonitrileYield 89%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of the product of Example 8f (1.54 g, 10.0 mmol) in thionyl chloride (6 mL) was heated to 84° C. overnight in a sealed vessel. The reaction mixture was cooled and then poured into ice-water (100 mL). The organics were extracted with diethyl ether (80 mL×4). The combined organic phase was washed with saturated aqueous sodium bicarbonate (160 mL×2) and brine (160 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound as a brown oil (1.20 g, Yield: 89%). 1H NMR (400 MHz, CDCl3) δ 2.45 (t, J=7.4 Hz, 2H), 1.96 (s, 3H), 1.80 (t, J=7.4 Hz, 2H), 1.17 (s, 6H) ppm.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe organics were extracted with diethyl ether (80 mL×4)
  3. washThe combined organic phase was washed with saturated aqueous sodium bicarbonate (160 mL×2) and brine (160 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e274bddb2f4e431ca30adc63579493b7
Source dataset
uspto-grants-2016_05
Patent number
US09353063B2

Reaction notes

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