Hydrochloric Acid → 2-(3-Formyl-2-thienyl)-4-methylbutyronitrile

HRID 1071630Notes

Reaction equation

HRID 1071630 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[CH:11]([CH2:14][CH2:15][CH3:16])[C:12]#[N:13].Cl>CC(C)=O.[Cl-].[Na+].O>[CH:2]([C:6]1[CH:10]=[CH:9][S:8][C:7]=1[CH:11]([CH2:14][CH2:15][CH3:16])[C:12]#[N:13])=[O:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 223936462-[3-(1,3-Dioxolan-2-yl)-2-thienyl]-4-methylbutyronitrile

Product 1

HCID 223935692-(3-Formyl-2-thienyl)-4-methylbutyronitrileYield 94.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

2.16 g (9.10 mmol) of 2-[3-(1,3-dioxolan-2-yl)-2-thienyl]-4-methylbutyronitrile was dissolved in 40 ml of acetone, 115 ml of 5N HCl was added, and the mixture was heated at 70° C. for 3 minutes. 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 magnesium sulfate and evaporated, to give a crude product. The crude product was subjected to 75 g of silica gel (ethyl acetate:hexane=1:2), to give 1.66 g (8.58 mmol, 94.3%) of the title compound as a brown 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 magnesium sulfate
  5. customevaporated
  6. customto give a crude product

Sources & evidence

ORD record
ord-7b6e4081b7b04928913534e264455d56
Source dataset
uspto-grants-2005_06
Patent number
US06906072B1

Reaction notes

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