Acetic Acid → 4-[(Pyrrolidin-1-yl)methyl]benzaldehyde

HRID 1820001Notes

Reaction equation

HRID 1820001 reaction equation
CO[CH:3]([O:12]C)[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[N:14]1([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([CH:3]=[O:12])=[CH:11][CH:10]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 24436Sodium SulfateHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 156262754-(Dimethoxymethyl)benzaldehyde

Product 1

HCID 230908284-[(Pyrrolidin-1-yl)methyl]benzaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(dimethoxymethyl)benzaldehyde (25.0 g, 120 mmol), pyrrolidine (10.0 ml, 120 mmol), acetic acid (6.87 ml, 120 mmol) and anhydrous sodium sulfate (34.1 g, 240 mmol) in dichloromethane (300 ml) was added sodium triacetoxyborohydride (38.2 g, 180 mmol), and the mixture was stirred for 3 days. Potassium carbonate was added to the reaction mixture, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate). 1N Hydrochloric acid (300 ml) was added to the obtained oil, and the mixture was washed with diethyl ether after 2 hrs. The aqueous layer was basified with potassium carbonate, and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate) to give the title compound (22.7 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washthe mixture was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate)
  7. addition1N Hydrochloric acid (300 ml) was added to the obtained oil
  8. washthe mixture was washed with diethyl ether after 2 hrs
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with saturated brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customthe obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate)

Sources & evidence

ORD record
ord-1e311c44640949f9a309c2ee399e52d2
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

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