Hydrochloric Acid → 3-Cyclobutyl-3-oxopropanenitrile

HRID 1914858Notes

Reaction equation

HRID 1914858 reaction equation
[H-].[Na+].[CH:3]1([C:7]([O-:9])=O)[CH2:6][CH2:5][CH2:4]1.[C:10](#[N:12])[CH3:11].Cl>C1COCC1.O>[CH:3]1([C:7](=[O:9])[CH2:11][C:10]#[N:12])[CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 6993960Cyclobutanecarboxylate

Product 1

HCID 138611153-Cyclobutyl-3-oxopropanenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 50 mL three necked round bottom flask containing NaH (980 mg, 60%, 24.50 mmol, 1.57 eq.) and THF (10 mL) was heated to reflux under nitrogen for about 30 min. Then a mixture of cyclobutanecarboxylate [CCLXVII] (2 g, 15.6 mmol, 1.00 eq.) and acetonitrile (1 g, 24.3 mmol, 1.56 eq.) in 20 mL of THF was added dropwise to the refluxing suspension. After addition, the resulting mixture was refluxed for 16 h and worked up with water. The pH value of the reaction solution was adjusted to 4 with aqueous HCl solution and extracted with ethyl acetate. The combined organic phases were dried and concentrated, the residue was applied onto a silica gel column with ethyl acetate/petroleum ether as the eluent to give Compound [CCLXVIII] as a yellow oil: 1H NMR (300 MHz, CDCl3) δ ppm 3.40-3.60 (m, 1H), 3.43 (s, 2H), 2.25-2.36 (m, 4H), 2.01-2.15 (m, 1H), 1.82-1.96 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for about 30 min
  3. additionwas added dropwise to the refluxing suspension
  4. additionAfter addition
  5. temperaturethe resulting mixture was refluxed for 16 h
  6. extractionextracted with ethyl acetate
  7. customThe combined organic phases were dried
  8. concentrationconcentrated
  9. customto give Compound [CCLXVIII] as a yellow oil

Sources & evidence

ORD record
ord-71b0809b337a4e69b3510110bca5c67b
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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