Acetic Acid → 321198-27-0

HRID 1386953Notes

Reaction equation

HRID 1386953 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1>[N:11]1([CH2:6][C:5]2[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=2)[C:1]#[N:2])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 90670m-FormylbenzonitrileHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21180390321198-27-0Yield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of of 3-cyanobenzaldehyde (15 g, 114.4 mmol) in THF (150 ml) was added pyrrolidine (9.76 g, 137.2 mmol, 1.2 eq.), acetic acid (8,24 g, 137.2 mmol, 1.2 eq.) and sodium triacetoxyborohydride (36.3 g, 171.6 mmol, 1.5 eq.). The resulting suspension was vigorously stirred at r.t. for 24 hrs. under Ar. 5% NaHCO3 was then added and the mixture stirred for a further 10-15 min. The mixture was then extracted with ethylacetate. The organic phase was washed with brine, then dried with Na2SO4. After removal of the solvent the yellow liquid was distilled over a Vigreux column to afford the title compound as a colorless liquid (19 g, 102 mmol, 89% yield). MS: m/e=186 (M+)

Workup

  1. stirringthe mixture stirred for a further 10-15 min
  2. extractionThe mixture was then extracted with ethylacetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried with Na2SO4
  5. customAfter removal of the solvent the yellow liquid
  6. distillationwas distilled over a Vigreux column

Sources & evidence

ORD record
ord-0eeae3ba7aa2480b9405ce9e09a8c2fa
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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