2-Bromopropane → 2-[3-(1,3-Dioxolan-2-yl)-2-thienyl]-4-methylbutyronitrile

HRID 1071629Notes

Reaction equation

HRID 1071629 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[CH2:11][C:12]#[N:13].Br[CH:15]([CH3:17])[CH3:16].[OH-].[K+]>CS(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+].O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[CH:11]([CH2:16][CH2:15][CH3:17])[C:12]#[N:13]

Participants

7

Reactant 3

HCID 63582-Bromopropane2×HCID 14797Potassium Hydroxide2×HCID 22393742HCID 22393742, compound

Product 1

HCID 223936462-[3-(1,3-Dioxolan-2-yl)-2-thienyl]-4-methylbutyronitrileYield 49.1%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

1.43 g (7.32 mmol) of 3-(1,3-dioxolan-2-yl)-2-thiopheneacetonitrile was dissolved in 2 ml of dimethyl sulfoxide, and 1.08 g (8.78 mmol) of 2-bromopropane, 100 mg (cat) of tetra-n-butylammonium iodide and 3 ml of 50% potassium hydroxide were successively added. After 25 minutes, 300 mg of 2-bromopropane, further after 50 minutes, 1 ml of 50% potassium hydroxide and 2 ml of DMSO were added. After completion of the reaction, brine was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated, to obtain a crude product. The crude product was subjected to 100 g of silica gel (ethyl acetate:hexane=1:8), to give 853 mg (3.59 mmol, 49.1%) of the title compound as a yellow oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customto obtain a crude product

Sources & evidence

ORD record
ord-9435d1ae152347c288965130f46f7a57
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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